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

Chem Commun (Camb)

Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan.

Published: December 2020

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.

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http://dx.doi.org/10.1039/d0cc07134jDOI Listing

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