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One-Step Synthesis of Acylboron Compounds via Cu-Catalyzed Carbonylative Borylation of Alkyl Halides

preprint
submitted on 17.08.2020 and posted on 18.08.2020 by Cheng Li-Jie, Zhao Siling, Neal Mankad
A Cu-catalyzed carbonylative borylation of unactivated alkyl halides has been developed, enabling efficient synthesis of aliphatic potassium acyltrifluoroborates (KATs) in high yields by treating the in-situ formed tetracoordinated acylboron intermediates with aqueous KHF2. A variety of functional groups are tolerated under the mild reaction conditions, and primary, secondary and tertiary alkyl halides are all applicable. In addition, this method also provides facile access to N-methyliminodiacetyl (MIDA) acylboronates as well as α-methylated potassium acyltrifluoroborates in a one-pot manner. Mechanistic studies indicate a radical atom transfer carbonylation (ATC) mechanism to form acyl halide intermediates that are subsequently borylated by (NHC)CuBpin.

Funding

NSF CHE-1664632

History

Email Address of Submitting Author

npm@uic.edu

Institution

University of Illinois at Chicago

Country

USA

ORCID For Submitting Author

0000-0001-6923-5164

Declaration of Conflict of Interest

none

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