Work

Ligand‐Controlled Regioselective Alkoxycarbonylation of Nonfunctionalized Unsymmetric Internal Alkynes

Year: 2024

Type: article

Abstract: Pd-catalyzed alkoxycarbonylation of internal alkynes provides a straightforward access to α,β-disubstituted acrylic esters. Compared with the well-established regioselective alkoxycarbonylation of terminal alkynes, the regioselective hydrocarboxylation of non-functionalized unsymmetric internal alkynes was more challenging owing to the delicate differences of properties between the two substituents. Herein, by using either monophosphine ligand based on 2,3-dihydrobenzo[d][1,3]oxaphosphole motif or bidentate ligand Ph-Phox, the regioselective alkoxycarbonylations of aryl-aryl, aryl-alkyl and alkyl-alkyl disubstituted alkynes were achieved, giving a diversity of trisubstituted α,β-unsaturated carboxylic esters with moderate to excellent yields and high regioselectivity. The synthetic utility of obtained α,β-disubstituted acrylic esters was demonstrated.

Source: Chemistry - A European Journal

DOI: 10.1002/chem.202404091

Authors: Bin Wang, Zhen Wang, Chaoren Shen, Kaiwu Dong

Institution: East China Normal University

Language: English

Topic: Catalytic Cross-Coupling Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: bronze

Funders: National Natural Science Foundation of China, Shanghai Municipal Education Commission, National Key Research and Development Program of China, Fundamental Research Funds for the Central Universities

Awards: G2623235406, G2633840602, G4833463889