Issue 15, 2022

Catalyst-controlled selective borocarbonylation of benzylidenecyclopropanes: regiodivergent synthesis of γ-vinylboryl ketones and β-cyclopropylboryl ketones

Abstract

Regioselective catalytic multi-functionalization reactions enable the rapid synthesis of complexed products from the same precursors. In this communication, we present a method for the regiodivergent borocarbonylation of benzylidenecyclopropanes with aryl iodides. Various γ-vinylboryl ketones and β-cyclopropylboryl ketones were produced in moderate to good yields with excellent regioselectivity from the same substrates. The choice of the catalyst is key for the regioselectivity control: γ-vinylboryl ketones were produced selectively with IPrCuCl and Pd(dppp)Cl2 as the catalytic system, while the corresponding β-cyclopropylboryl ketones were obtained in high regioselectivity with Cu(dppp)Cl, [Pd(η3-cinnamyl)Cl]2 and xantphos as the catalytic system. Moreover, γ-vinylboryl ketones and β-cyclopropylboryl ketones were successfully transformed into several other value-added products.

Graphical abstract: Catalyst-controlled selective borocarbonylation of benzylidenecyclopropanes: regiodivergent synthesis of γ-vinylboryl ketones and β-cyclopropylboryl ketones

Supplementary files

Article information

Article type
Edge Article
Submitted
10 Feb 2022
Accepted
18 Mar 2022
First published
21 Mar 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2022,13, 4321-4326

Catalyst-controlled selective borocarbonylation of benzylidenecyclopropanes: regiodivergent synthesis of γ-vinylboryl ketones and β-cyclopropylboryl ketones

F. Wu and X. Wu, Chem. Sci., 2022, 13, 4321 DOI: 10.1039/D2SC00840H

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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