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submitted on 17.08.2020 and posted on 18.08.2020by 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