Palladium-Catalyzed One-Step Synthesis of Stereodefined Difunctionalized Glycals
Year: 2022
Type: article
Abstract: Open AccessCCS ChemistryRESEARCH ARTICLE11 May 2022Palladium-Catalyzed One-Step Synthesis of Stereodefined Difunctionalized Glycals Xiao-Ping Gong†, Yuke Li†, Hong-Chao Liu, Zhe Zhang, Zhi-Jie Niu, Ya-Nan Ding, Yang An, Xi Chen, Yan-Chong Huang, Rui-Qiang Jiao, Xue-Yuan Liu and Yong-Min Liang Xiao-Ping Gong† State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 , Yuke Li† Department of Chemistry, Centre for Scientific Modeling and Computation, Chinese University of Hong Kong, Shatin, Hong Kong 999077 , Hong-Chao Liu State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 , Zhe Zhang State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 , Zhi-Jie Niu State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 , Ya-Nan Ding State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 , Yang An State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 , Xi Chen State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 , Yan-Chong Huang State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 , Rui-Qiang Jiao State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 , Xue-Yuan Liu *Corresponding authors: E-mail Address: [email protected] E-mail Address: [email protected] State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 and Yong-Min Liang *Corresponding authors: E-mail Address: [email protected] E-mail Address: [email protected] State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 https://doi.org/10.31635/ccschem.022.202201794 SectionsSupplemental MaterialAboutAbstractPDF ToolsAdd to favoritesDownload CitationsTrack Citations ShareFacebookTwitterLinked InEmail Efficiently modifying glycals by directly introducing functional groups into their double bonds is a long-standing challenge. Here, the strategy of introducing two different functional groups into 1-iodoglycals to obtain modified glycals in one step through palladium catalysis was reported for the first time, and the modified glycals contained stereodefined tetrasubstituted olefins. Using this method, various difunctionalized glycals that were difficult to form by other routes were synthesized in moderate to good yields. Control experiments and density functional theory calculations show that the palladium catalyst played dual roles in this transformation, namely, inducing nucleophilic substitution and catalyzing Suzuki coupling. The reaction intermediate was isolated and confirmed by X-ray crystallographic analysis. Furthermore, the gram-scale synthesis and facile deprotection of the target compound enhances the practicality of this strategy. Download figure Download PowerPoint Introduction Tetrasubstituted olefins have attracted tremendous attention because their fundamental structural motifs are found in numerous biologically active compounds.1,2 To date, many transition-metal-catalytic processes for constructing tetrasubstituted olefins have been reported.3–8 Of all the excellent work in this area, the introduction of two different functional groups in one step to synthesize stereodefined tetrasubstituted alkenes is particularly striking. In pioneering work by Dong's group,9 norbornene and palladium were employed as cocatalysts to prepare unsymmetrical tetrasubstituted regular olefins (Scheme 1a). In addition, the Catellani reaction of some partially aromatic olefins was also reported to produce tetrasubstituted olefins.10–12 Here, a complementary strategy for tetrasubstituted olefin synthesis was sought through introducing an acyl and aryl by using palladium catalysis in one step. Scheme 1 | Some reported reactions and design of this reaction. Download figure Download PowerPoint C-Glycals, which belong to a subclass of C-glycosides, contain a double bond that can be transformed into various functional groups, and they have attracted the interest of numerous researchers in recent years.13–18 To date, a plethora of cross-coupling reactions catalyzed by transition metals have been employed for the conversion or modification of C-glycals.19–32 Compared with the strategy of realizing glycal conversion by functionalizing the double bond, modifying glycals can retain the unsaturated bond, which will increase the possibility of late-stage functionalization to construct useful and complicated glycosides. Most methods of modifying glycals can be separated into two strategies: (1) C-1 functionalization and (2) C-2 functionalization. Two methods have been reported to introduce functional groups at the C-1 position (Scheme 1b1). One is to prefunctionalize the C–H bond at the C-1 position and then introduce the functional group by cross-coupling,33–35 and the other is to introduce a directing group at the C-2 position to achieve transition-metal-catalyzed C–H functionalization at the C-1 position.36 Similarly, C-2 functionalization can also be achieved in two ways (Scheme 1b2), namely, transition-metal-catalyzed direct C–H functionalization37,38 and catalytic functionalization followed by C–H bond prefunctionalization at the C-2 position.39–42 However, to the best of our knowledge, introducing two different motifs in one step to realize glycal difunctionalization has not yet been reported. Scheme 2 | Control experiments. aThe standard condition refers to Pd(OAc)2 (10 mol %), TFP (20 mol %), and Cs2CO3 (1.5 equiv) reacted at 105 °C for 14 h. Download figure Download PowerPoint Combining our interest in palladium catalysis with the knowledge that the nucleophilic 3,4-dihydro-2H-pyran moieties in glycals can directly couple to electrophilic groups without a transition-metal catalyst,43–46 we envisioned that the bifunctionalization of glycals could be realized by introducing electrophilic groups through the nucleophilicity of 3,4-dihydro-2H-pyran (Scheme 1c) and the use of a transition metal to attract nucleophilic groups for catalytic coupling. However, using the nucleophilicity of pyran analogs to realize the functionalization of glycals has only been reported for a few relatively simple atoms or groups, such as Cl, Br, I, and NO2.47–49 It could be that the steric hindrance between the protective groups on the sugar and the substrate makes functionalization difficult. Inspired by the Zimmerman–Traxler model,50 the coordination metal not only regulates the geometry of the product but also promotes the transformation by shortening the distance between the reactants.51,52 Therefore, we proposed that a palladium atom could be introduced into the C-1 position to shorten the distance between the sugar and the electrophilic reagent through its coordination for realizing the functionalization of C-2. Then, the palladium-catalyzed cross-coupling reaction could be performed to achieve C-1 functionalization. And finally, the difunctionalization of the 1-iodoglycal could be realized in one step (Scheme 1d). However, despite being strategically intriguing, considerable challenges have to be considered: (1) how to achieve the C-2 functionalization via transition-metal-induced functionalization; (2) how to control the process to realize C-2 site functionalization prior to C-1 site coupling instead of direct C-1 site coupling; and (3) how the increased steric hindrance after introducing an electrophilic group into the double bond would affect the subsequent cross-coupling. Experimental Methods 1( a–d) (0.1 mmol), Pd(OAc)2 (10 mol %), TFP (20 mol %), and Cs2CO3 (1.5 equiv) were added to an oven-dried tube equipped with a stirring bar. The tube was charged with argon five times. (The tube was sealed with a tipping plug.) 3( a–o) (4.5 equiv) and 1,4-dioxane (1 mL) were added to the reaction tube one after another. The resulting suspension was stirred vigorously at room temperature for 10 min before being placed in a preheated oil bath at 105 °C and stirred for another 10 min. Then 2( a–v) (1.5 equiv) dissolved in 1 mL of 1,4-dioxane was injected into the tube and stirred for another 14 h at 105 °C. Upon completion of the reaction, the mixture was filtered through a thin pad of silica gel. The filter cake was washed with ethyl acetate, and the combined filtrate was concentrated. The residue was purified by preparative thin layer chromatography or flash column chromatography on silica gel to yield the desired product. (Note: Feed sequence, temperature control, and purity of 1( a–d) are important for the reproducibility of this procedure.) Results and Discussion As an initial trial, we performed the reaction with triisopropylsilyl-protected 1-iodoglucal ( 1a), phenylboronic acid ( 2a), and acetic anhydride ( 3a), using Pd(OAc)2 as the catalyst, PPh3 as the ligand, and Cs2CO3 as the base to obtain the corresponding difunctionalized glycal ( 4aaa) (Table 1). A trace amount of product 4aaa was obtained using 1,4-dioxane as the solvent (entry 1). Furthermore, the yield of byproduct 4aa formed by 1a and 2a via Suzuki coupling was 15%. Encouraged by these results, we optimized the conditions of this reaction. Palladium catalysts were first investigated, and other palladium sources were shown to have minor effects on the outcome of this reaction (entries 2 and 3). Next, the ligand influence was tested, and the results show that the yield of the reaction was significantly affected by the ligand (entries 4–7). Of the tested ligands, tri(2-furyl)phosphine (TFP) was better than others (entry 4), and up to 45% yield was obtained. Following the above investigations, bases were screened, and we found that they had relatively insignificant effects (entries 8–11). At this point, the highest yield was only 45%, so we investigated the solvent effect. However, changing the solvent did not increase the yields (entries 12–15), even though yields of 40% were obtained with MeCN (entry 13). Based on the characteristics of the reaction and the side reaction of 1a and 2a, direct coupling was not effectively inhibited. Consequently, we tried to add phenylboronic acid at the end of this process (entry 16). Surprisingly, when phenylboronic acid ( 2a) was added after 1a, 3a, Pd(OAc)2, P(2-furyl)3, and Cs2CO3 were stirred at 105 °C for 10 min, the isolated yield reached 78%. When reducing the catalytic loading to 0.05 equiv, the reaction still provided 4aaa in 71% yield (entry 17). In addition, changing the temperature did not improve the yield of 4aaa (see Supporting Information Table S1). Table 1 | Optimization of Reaction Conditionsa Entry Catalyst Ligand Base Solvent Yield of 4aaa (%) Yield of 4aa (%) 1 Pd(OAc)2 PPh3 Cs2CO3 1,4-Dioxane 5 15 2 Pd(PPh3)4 PPh3 Cs2CO3 1,4-Dioxane n.d. 25 3 PdCl2 PPh3 Cs2CO3 1,4-Dioxane n.d. 10 4 Pd(OAc)2 P(2-furyl)3 Cs2CO3 1,4-dioxane 45 33 5 Pd(OAc)2 P(p-CF3 C6H4)3 Cs2CO3 1,4-Dioxane 22 18 6 Pd(OAc)2 P(p-Tol)3 Cs2CO3 1,4-Dioxane 16 10 7 Pd(OAc)2 P(p-FC6H4)3 Cs2CO3 1,4-Dioxane Trace Trace 8 Pd(OAc)2 P(2-furyl)3 K2CO3 1,4-Dioxane 15 22 9 Pd(OAc)2 P(2-furyl)3 Na2CO3 1,4-Dioxane Trace Trace 10 Pd(OAc)2 P(2-furyl)3 NaOtBu 1,4-Dioxane Trace Trace 11 Pd(OAc)2 P(2-furyl)3 KOAc 1,4-Dioxane 10 14 12 Pd(OAc)2 P(2-furyl)3 Cs2CO3 Toluene Trace 60 13 Pd(OAc)2 P(2-furyl)3 Cs2CO3 MeCN 40 4 14 Pd(OAc)2 P(2-furyl)3 Cs2CO3 1,2-Dichlorethan 6 56 15 Pd(OAc)2 P(2-furyl)3 Cs2CO3 N,N-dimethylformamide Trace Trace 16b Pd(OAc)2 P(2-furyl)3 Cs2CO3 1,4-Dioxane 81 (78)c 5 17b,d Pd(OAc)2 P(2-furyl)3 Cs2CO3 1,4-Dioxane 71 Trace aAll reactions were performed on 0.1 mmol scale. Yield were determined by 1H NMR analysis using 1,3,5-Trimethoxybenzene as the internal standard. b 1a, 3a, Pd(OAc)2, P(2-furyl)3, and Cs2CO3 stirred at 105 °C for 10 min, and then 2a was added. cIsolated yield. dHalf of Pd(OAc)2 (5 mol %) and half of P(2-furyl)3 (10 mol %) were used. With optimized reaction conditions established, the scope of arylboronic acids was examined next, as shown in Table 2(a). First, we used p, m, and o-tolylboronic acid ( 4aba, 4ama, and 4apa) to investigate the effect of the substituent position on the yield. The results show that the para- and meta-substituted compounds were compatible with this method, whereas the yield of the ortho-substituted compound was low, possibly due to the steric hindrance of the ortho-substituted methyl with acyl or protective group. A range of para- and meta-substituted arylboronic acids bearing electron-donating and electron-withdrawing groups was tolerated and afforded the corresponding aryl-substituted 1-iodoglycals in moderate to good yields ( 4aba- 4aoa). Among the tested substituents, halides (F, Cl, and Br) ( 4aea– 4aga) were well tolerated and could serve as new reaction sites for the further modification of the difunctionalized 1-iodoglycals. Moreover, disubstituted arylboronic acids were also tested in this transformation. Although the yield of 3,5-dimethylphenylboronic acid was moderate ( 4asa), the yields of 3,5-difluorophenylboronic acid ( 4aqa) and 3,5-dichlorophenylboronic acid ( 4ara) reached up to 83% and 82%, respectively. The activities of other types of boric acids in the reaction were also explored, and the results show that heterocyclic arylboronic and alkenylboronic acids were compatible with this reaction ( 4ata- 4ava), even though the yields were unsatisfactory. Table 2 | Reaction Scope of Arylboronic Acids, Aliphatic Anhydrides, and 1-Iodoglycalsa aAll reactions were performed on a 0.1 mmol scale. Order of addition was 1a, 3a, Pd(OAc)2, TFP, and Cs2CO3 dissolved in 1 mL of 1,4-dioxane. After stirring at 105 °C for 10 min, 2a dissolved in 1 mL of 1,4-dioxane was added. Reported yields are for the isolated products. bThe reaction was run with 3 mmol scale. The order of addition was 1a, 3a, Pd(OAc)2, TFP, and Cs2CO3 dissolved in 32 mL of 1,4-dioxane. After stirring at 105 °C for 10 min, 2a dissolved in 8 mL of 1,4-dioxane was added. cThis refers to the yield of removing protective groups by the reaction of 4aaa with TBAF. Next, we evaluated the scope of anhydrides, as shown in Table 2(b). Lower saturated fatty anhydrides underwent this transformation to obtain difunctionalized 1-iodoglycals in moderate to good yields ( 4aaa– 4aah). Then, when higher fatty anhydrides such as stearic anhydride and oleic anhydride were used, satisfactory yields were obtained ( 4aai– 4aaj). To further investigate the scope of anhydrides in these reaction, we employed a branched anhydride in the reaction ( 4aak). Due to steric hindrance, an acceptable yield was obtained. Because of the widespread presence of phenylpropionyl moieties in various drugs and natural products,53,54 we explored the tolerance of phenylpropionic anhydride and its derivatives to the reaction ( 4aal– 4aao). In particular, the isolated yield of 4ala from 3-phenylpropionic anhydride achieved up to 80%. In this part, in order to verify the practicability of this reaction, we performed the reaction with 3 mmol scale and obtained 4aaa 1.78 g. In addition, the reaction of 4aaa with tetrabutylammonium fluoride (TBAF) under mild conditions efficiently obtained deprotected difunctionalized 1-iodoglycals. To further examine the scope of 1-iodoglycals, the coupling reactions of 1-iodoglycals 1b, 1c, and 1d, which were derived from l-rhamnose, d-galactose, and d-xylose, respectively, with different anhydrides and arylboronic acids were performed under standard conditions (Table 2c). Obviously, 1-iodoglycals 1b reacted with different aliphatic anhydrides and arylboronic acids under standard conditions, and the yields of modified 1-iodoglycals 1b, which originated from l-rhamnose, were satisfactory ( 4baa, 4bab, 4bad, 4bia, and 4bla). Furthermore, under standard conditions, 1c reacted with different anhydrides and phenylboronic acid with different substituents to give moderate yields ( 4caa, 4cac, 4cai, 4cqa, and 4cra). Notably, the previously unreported 1d was also compatible with this reaction ( 4daa, 4dja, and 4dka). We have tried to synthesize 1-iodoglycals with other substrates, such as l-fucose, d-ribose, and l-ribose. However, their corresponding 1-iodoglycals are unstable and decomposed when purified on silica gel column. In addition, attempts were also made to replace the protective group of 1-iodoglycals, but the corresponding 1-iodoglycal product was not obtained. To gain insight into the reaction mechanism, a series of control experiments were conducted (Scheme 2). First, the reaction in Schemes 2a and 2b show that 1-iodoglycals and 1-phenylglycals could not be directly acylated at C-2. Furthermore, the combination of Schemes 2b and 2c indicate that an acyl group is likely to be introduced first in the reaction, and then an aryl group is added. Scheme 2c also shows that the acyl groups cannot be introduced when palladium is not directly connected to glycals, despite the fact that palladium atoms exist in the reaction system. To further verify this process, we reacted 1a with 3a under standard conditions, except with amounts of Pd(OAc)2 and TFP equal to that of the substrate. To our delight, we obtained a yellow compound, and determined its structure by single-crystal X-ray diffraction (Scheme 2d). The compound could be directly coupled with phenylboronic acid under standard conditions (Scheme 2e) and could replace Pd(OAc)2 and TFP to catalyze the reaction (Scheme 2f). This data established that T-2 was a catalytically competent species. Its presence demonstrated that an acyl group was introduced first, and then an aryl group was coupled in the reaction. This result was also consistent with the initial assumption (vide supra). Next, in order to know whether the acyl group introduction was affected by palladium atoms, we used 1a, Pd(OAc)2, and TFP as the raw materials, and then we obtained the oxidation addition product ( T-1) and confirmed its structure using nuclear magnetic resonance (NMR) spectra and high resolution mass spectrum (Scheme 2g). Next, the intermediate T-2 was obtained by the reaction of T-1 with acetic anhydride and base (Scheme 2h). This result combined with Scheme 2a shows that the introduction of the acyl group is affected by palladium atoms. In order to clearly know the process of introducing the acyl group into the 1-iodoglycals under the influence of palladium, density functional theory (DFT) calculations were employed to study the energy changes in this process. At the beginning, the molecule 1a interacts with the PdL2, and the ligand L leaves to generate B, releasing 1.5 kcal/mol energy. Next, the oxidative addition process occurs via C-ts with a small barrier of about 3.4 kcal/mol energy, and 5.7 kcal/mol energy releases to form D. After that, Cs2CO3 attacks the Pd center of D, which results in E releasing 28.1 kcal/mol energy. After 2a coordinates the Pd center of E with the release of 15.5 kcal/mol energy, the C–C bond forms via G-ts with a 20.4 kcal/mol energy barrier to generate 5-member ring complex H with 5.6 kcal/mol energy increasing. And, C–H bond breaking occurs through I-ts with a barrier of about 16.4 kcal/mol energy, and then J generates with the release of 11.4 kcal/mol energy. (The energy barrier that the C–O bond first broke and subsequent C–H activation is detailed in Supporting Information Figure S1.) The C–O bond breaking through a fairly small barrier with 3.6 kcal/mol energy leads to M with the release of 9.3 kcal/mol energy. In the end, CsHCO3 and CH3COOCs leave, and reaction intermediate T-2 generates. In the whole process, the rate-determining step (rds) is the barrier from F to I-ts with 22.0 kcal/mol energy. In addition, the kinetic isotope effects (KIE) experiment shows that C–H activation is not the rate-determining step (see Figure 1 and Supporting Information Table S2). Figure 1 | Computed Gibbs-free energy profile of introduced acyl step in palladium-catalyzed one-step synthesis of stereodefined difunctionalized glycals. The relative free energies are presented in kcal/mol. Download figure Download PowerPoint Based on the above control experiments and DFT calculations, we propose the following reaction cycle process (Scheme 3). First, the direct oxidative addition of the Pd(0) complex I to 1-iodoglycal 1 gives Pd(II) intermediate II. Next, II undergoes a ligand substitution process with anhydride 3 to generate hybrid Pd complex III, which is subsequently converted to hybrid oxyonium Pd(II) complex IV via palladium-induced nucleophilic attack. Then, Pd(II) intermediate IV reacts with base to eliminate H atoms, and then CH3COO− leaves to form intermediate V. The subsequent Suzuki coupling reaction of V with an arylboronic acid 2 yields 4 and regenerates I. Scheme 3 | Proposed catalytic cycle. Download figure Download PowerPoint Conclusion A Pd-catalyzed one-step synthesis method for constructing modified glycals containing stereodefined tetrasubstituted olefins was developed. In this transformation, palladium plays a dual role in mediating inner-sphere C–C coupling and serving as a Lewis acid to promote carbonyl addition, as demonstrated by control experiments and DFT calculations. The reaction is operationally simple, proceeds under mild conditions, and represents the first use of a simple prefunctionalized glycal in difunctionalization reactions. This approach thus offers a route to synthesis of 1,2-di-C-substituted glycals, which are difficult to obtain by other methods. Further studies of the efficient modification of glycals or glycosides are ongoing in our group. Supporting Information Supporting Information is available and includes experimental details, X-ray crystallography structures of compounds 4aca, 4ada (Table 2a), and 4aaa (Table 2b) and T-2 (Scheme 2). Conflict of Interest There is no conflict of interest to report. Funding Information We thank the National Natural Science Foundation of China (NSF 22171114 and 21772075) for its financial support. And the computations reported in this paper were performed on the computer clusters at the Centre for Scientific Modeling and Computation at the Chinese University of Hong Kong. References 1. Flynn A. B.; Ogilvie W. W.Stereocontrolled Synthesis of Tetrasubstituted Olefins.Chem. Rev.2007, 107, 4698–4745. Google Scholar 2. Mukherjee N.; Planer S.; Grela K.Formation of Tetrasubstituted C–C Double Bonds via Olefin Metathesis: Challenges, Catalysts, and Applications in Natural Product Synthesis.Org. Chem. Front.2018, 5, 494–516. Google Scholar 3. Ping Y.; Wang Wang Wang of from through Chem. Google Scholar Synthesis of Tetrasubstituted via and Google Scholar of Chem. 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Source: CCS Chemistry
Authors: Xiao-Ping Gong, Yuke Li, Hong-Chao Liu, Zhe Zhang, Zhi-Jie Niu, Ya-Nan Ding, Yang An, Xi Chen, Yan-Chong Huang, Rui-Qiang Jiao, Xue-Yuan Liu, Yong-Min Liang
Institutions: Lanzhou University, Chinese University of Hong Kong
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: diamond
OpenAlex ID: W4225761945