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Copper(I)-Catalyzed Boryl Substitution of 1-Trifluoromethyl Allenes for the Synthesis of 3-Boryl-Substituted 1,1-gem-Difluorodienes
| Title: | Copper(I)-Catalyzed Boryl Substitution of 1-Trifluoromethyl Allenes for the Synthesis of 3-Boryl-Substituted 1,1-gem-Difluorodienes |
| Authors: | Akiyama, Sota Browse this author | | Nomura, Syogo Browse this author | | Kubota, Koji Browse this author | | Ito, Hajime Browse this author →KAKEN DB |
| Issue Date: | 4-Feb-2020 |
| Publisher: | American Chemical Society |
| Journal Title: | Journal of organic chemistry |
| Volume: | 85 |
| Issue: | 6 |
| Start Page: | 4172 |
| End Page: | 4181 |
| Publisher DOI: | 10.1021/acs.joc.9b03353 |
| Abstract: | A method to synthesize 3-boryl-1,1-gem-difluorodienes via the copper(I)-catalyzed boryl substitution of trifluoromethyl-substituted allenes was developed. The borylated compounds were obtained up to 91% yield with excellent selectivity. We proposed that the reaction proceeded via gamma-selective borylcupration into the trifluoromethyl-substituted alien; followed by copper(I)-beta-fluoro elimination. Subsequent transformations of the borylation product by Suzuki-Miyaura cross-coupling or Diels-Alder reaction provided various compounds bearing a difluoro moiety, which are difficult to synthesize by existing methods. |
| Rights: | This document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of organic chemistry, copyright c American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/doi/10.1021/acs.joc.9b03353. |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/80568 |
| Appears in Collections: | 総合化学院 (Graduate School of Chemical Sciences and Engineering) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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Submitter: 秋山 颯太
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