Three‐Component Gallium(III)‐Promoted Addition of Halide Anions and Acetylenes to Donor–Acceptor Cyclopropanes. Issue 32 (17th July 2018)

• Record Type: Journal Article
• Authors: Novikov, Roman A.; Borisov, Denis D.; Tarasova, Anna V.; Tkachev, Yaroslav V.; Tomilov, Yury V.
• Is Part Of: Angewandte Chemie international edition. Volume 57:Issue 32(2018)
• Page Start: 10293
• Page End: 10298
• Publication Date: 2018-07-17
• Subjects: alkynes -- donor–acceptor cyclopropanes -- gallium halides -- trans addition -- vinyl halides; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201803541
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: A new strategy for the three‐component addition of halide anions and acetylenes to donor–acceptor cyclopropanes (DACs) is presented. This reaction, which occurs with high E selectivity, is promoted by gallium(III) salts and based on the 1, 2‐zwitterionic reactivity of DACs. It opens up a new group of processes involving DACs. The reaction occurs readily with a broad range of substrates and is tolerant of various functional groups. This methodology makes it possible to assemble highly functionalized vinyl halides, which are very convenient building blocks in organic synthesis. A possible mechanism of this reaction and its stereochemical aspects are discussed in detail. Abstract : Special gal : A reaction for the three‐component addition of halide anions and acetylenes to donor–acceptor cyclopropanes (DAC) was promoted by gallium(III) salts in an approach based on 1, 2‐zwitterionic DAC reactivity and occurred with high E selectivity (see scheme). This methodology makes it possible to assemble highly functionalized vinyl halides, which are very useful building blocks in organic synthesis.