Work

Stereospecific Cu(I)-Catalyzed C–O Cross-Coupling Synthesis of Acyclic 1,2-Di- and Trisubstituted Vinylic Ethers from Alcohols and Vinylic Halides

Year: 2023

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide CuI and trans - N, N′ -dimethylcyclohexyldiamine catalyze the single-step C–O bond cross-coupling between 1,2-di- and trisubstituted vinylic halides with functionalized alcohols, producing acyclic vinylic ethers. This stereospecific transformation selectively gives each of the ( E )- and ( Z ) - vinylic ether products from the corresponding vinyl halide precursors. This method is compatible with carbohydrate-derived primary and secondary alcohols and several other functional groups. The conditions are mild enough to reliably generate vinylic allylic ethers without promoting Claisen rearrangements.

Source: Organic Letters

DOI: 10.1021/acs.orglett.3c01849

Authors: San L. Pham, Taehee Kim, Frank E. McDonald

Institution: Emory University

Language: English

Topic: Catalytic Cross-Coupling Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $5,000

Funders: Curtin University of Technology, National Institutes of Health, National Institute of General Medical Sciences