Radical Monofluoroalkylative Alkynylation of Olefins by a Docking-Migration Strategy.

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Tytuł:: Radical Monofluoroalkylative Alkynylation of Olefins by a Docking-Migration Strategy.
Autorzy:: Wang M; Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu, 215123, China.
Zhang H; Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu, 215123, China.
Liu J; Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu, 215123, China.
Wu X; Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu, 215123, China.
Zhu C; Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, 199 Ren-Ai Road, Suzhou, Jiangsu, 215123, China.
Źródło:: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2019 Dec 02; Vol. 58 (49), pp. 17646-17650. Date of Electronic Publication: 2019 Oct 21.
Typ publikacji:: Journal Article; Research Support, Non-U.S. Gov't
Język:: English
Imprint Name(s):: Publication: <2004-> : Weinheim : Wiley-VCH
Original Publication: Weinheim/Bergstr. : New York, : Verlag Chemie ; Academic Press, c1962-
MeSH Terms:: Alkenes/*chemistry
Alkynes/*chemistry
Bromosuccinimide/chemistry ; Catalysis ; Fluorine Compounds/chemistry ; Free Radicals/chemistry ; Molecular Structure ; Structure-Activity Relationship ; Temperature
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Grant Information:: 21722205 International National Natural Science Foundation of China; 21971173 International National Natural Science Foundation of China
Contributed Indexing:: Keywords: alkenes; alkynylation; difunctionalization; monofluoroalkylation; radical reactions
Substance Nomenclature:: 0 (Alkenes)
0 (Alkynes)
0 (Fluorine Compounds)
0 (Free Radicals)
K8G1F2UCJF (Bromosuccinimide)
Entry Date(s):: Date Created: 20191001 Date Completed: 20200923 Latest Revision: 20200923
Update Code:: 20240105
DOI:: 10.1002/anie.201910514
PMID:: 31566862
: Czasopismo naukowe

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A radical-mediated monofluoroalkylative alkynylation of alkenes is disclosed for the first time. The reaction demonstrates a remarkably broad substrate scope in which both activated and unactivated alkenes are suitable starting materials. The concurrent addition of an alkynyl and a monofluoroalkyl group onto an alkene proceeds through a docking-migration sequence, affording a vast array of valuable fluoroalkyl-substituted alkynes. Many complex natural products and drug derivatives are readily functionalized, demonstrating that this method can be used for late-stage alkynylation.
(© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)

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