Synthesis of functionalized cyclopropylboronic esters based on a 1,2-metallate rearrangement of cyclopropenylboronate.

Synthesis of functionalized cyclopropylboronic esters based on a 1,2-metallate rearrangement of cyclopropenylboronate.
Chem Commun (Camb). 2020 Nov 26;:
Authors: Mizoguchi H, Seriu M, Sakakura A
Abstract
A procedure converting tribromocyclopropane to densely functionalized β-selenocyclopropylboronic ester using the 1,2-metallate rearrangement of a boron ate-complex has been developed. Treatment of an in situ-generated cyclopropenylboronic ester ate-complex with phenylselenenyl chloride triggered stereospecific rearrangement to produce functionalized cyclopropanes. DFT calculations for 1,2-metallate rearrangement suggested that the reaction proceeds through a seleniranium intermediate.
PMID: 33241828 [PubMed - as supplied by publisher]

Source: Chemical Communications - November 26, 2020 Category: Chemistry Authors: Mizoguchi H, Seriu M, Sakakura A Tags: Chem Commun (Camb) Source Type: research