Open AccessAtom-Economical Ni-Catalyzed Diborylative Cyclization of Enynes: Preparation of Unsymmetrical Diboronates
Author(s) -
Natalia CabreraLobera,
M. Teresa Quirós,
William W. Brennessel,
Michael L. Neidig,
Elena Buñuel,
Diego J. Cárdenas
Publication year - 2019
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.9b02485
Subject(s) - enyne , chemistry , catalysis , reagent , combinatorial chemistry , alkyl , scope (computer science) , oxidative addition , atom (system on chip) , atom economy , reaction conditions , medicinal chemistry , organic chemistry , computer science , embedded system , programming language
We report a Ni-catalyzed diborylative cyclization of enynes that affords carbo- and heterocycles containing both alkyl- and alkenylboronates. The reaction is fully atom-economical, shows a broad scope, and employs a powerful and inexpensive catalytic Ni-based system. The reaction mechanism seems to involve activation of the enyne by Ni(0) through oxidative cyclometalation of the enyne prior to diboron reagent activation. An unprecedented dinuclear bis(organometallic) Ni(I) intermediate complex was isolated.