(2-Fluoroallyl)boration of Ketones with (2-Fluoroallyl)boronates

(2-Fluoroallyl)boration of Ketones with (2-Fluoroallyl)boronates Full article

Journal

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Output data

Year: 2020, Volume: 85, Number: 10, Pages: 6295-6308 Pages count : 14 DOI: 10.1021/acs.joc.9b03445

Authors

Novikov Maxim A. ¹ , Bobrova Angelina Yu. ^2,1 , Mezentsev Igor A. ^2,1 , Medvedev Michael G. ¹ , Tomilov Yury V. ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation
2	Higher Chemical College of the Russian Academy of Sciences, D. I. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya pl., 125047 Moscow, Russian Federation

Efficient routes toward activation of gem-chlorofluorocyclopropane-derived (2-fluoroallyl)boronates for allylboration of various ketones including functionalized and low-reactive ones were developed. Increasing the boron electrophilicity by the transformation of a boronate moiety into a borinic ester with nBuLi/trifluoroacetic anhydride (TFAA) makes (2-fluoroallyl)boration of acetyl arenes/hetarenes and aliphatic ketones possible with high diastereoselectivity. For low-reactive or sterically hindered ketones (e.g., benzophenone, adamantanone), “CuF”-based catalysts were developed: (NHC)CuF·HF and (NHC)CuOTf in the presence of an excess of KHF2 (NHC = IPr, SIPr, IPrCl).

Novikov M.A. , Bobrova A.Y. , Mezentsev I.A. , Medvedev M.G. , Tomilov Y.V.
(2-Fluoroallyl)boration of Ketones with (2-Fluoroallyl)boronates
Journal of Organic Chemistry. 2020. V.85. N10. P.6295-6308. DOI: 10.1021/acs.joc.9b03445 WOS Scopus OpenAlex

≡ Web of science:	WOS:000535303300006
≡ Scopus:	2-s2.0-85087701394
≡ OpenAlex:	W3016786429