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A Dual CuH- and Pd-Catalyzed Stereoselective Synthesis of Highly Substituted 1,3-Dienes

Year: 2021
Type: article
Abstract: Conjugated dienes are versatile building blocks and prevalent substructures in synthetic chemistry. Herein, we report a method for the stereoselective hydroalkenylation of alkynes, utilizing readily available enol triflates. We leveraged an in situ generated and geometrically pure vinyl-Cu(I) species to form the Z,Z- or Z,E-1,3-dienes in excellent stereoselectivity and yield. This approach allowed for the synthesis of highly substituted Z-dienes, including pentasubstituted 1,3-dienes, which are difficult to prepare by existing approaches.
DOI: 10.1021/acs.orglett.1c03324
Language: English
Field: Chemistry
Open Access status: green
Funders: National Science Foundation, Arnold and Mabel Beckman Foundation, Massachusetts Institute of Technology, Dalian Polytechnic University, National Institutes of Health, National Institute of General Medical Sciences, Division of Graduate Education
Awards: G236542531, Graduate Research Fellowship Program, G5662436926, G9000175394, Proteomics and model organism humanization to decode human genetics, Metal-Catalyzed Methods for Organic Synthesis
OpenAlex ID: W3208557844
FWCI: 1.485
Cites: 65
Cited by: 20
Related to: 10