Palladium-catalyzed regioselective and stereo-invertive ring-opening borylation of 2-arylaziridines with bis(pinacolato)diboron: experimental and computational studies.

ABSTRACT: A palladium catalyzed regioselective borylative ring opening reaction of 2-arylaziridines to give β-amino-β-arylethylborates was developed. The reaction reported herein represents the first example of ring-opening borylation of non-vinylic aziridines and direct borylative C(sp³)-N bond cleavage of neutral organic substrates. NMR studies and density functional theory (DFT) calculations suggested that the active intermediate for the reaction is a PdL₂ complex [L = P(t-Bu)₂Me]. The multi-component artificial force-induced reaction method (MC-AFIR) located the transition states for the regioselectivity-determining aziridine ring opening that proceeds in an S_N2 fashion, and explained the selectivity of the reaction. The full catalytic cycle con

SUBMITTER: Takeda Y 

PROVIDER: S-EPMC6024180 | biostudies-literature | 2016 Sep

REPOSITORIES: biostudies-literature