Issue 5, 2022

Rhodium-catalyzed sequential B(3)-, B(4)-, and B(5)-trifunctionalization of o-carboranes with three different substituents

Abstract

A rhodium-catalyzed one-pot trifunctionalization of o-carboranes with three different substituents via a carboxy group directed sequential B(5)-alkenylation, B(4)-alkyne annulation and B(3)-acyloxylation has been developed for the first time, leading to the synthesis of a new class of B(3,4,5)-trisubstituted o-carborane derivatives. Treatment of 1-COOH-2-CH3-o-C2B10H10 with ArC[triple bond, length as m-dash]CAr in the presence of a [Cp*RhCl2]2 catalyst and a Cu(OPiv)2 oxidant gave 1,4-[COOC(Ar)[double bond, length as m-dash]C(Ar)]-2-Me-3-OPiv-5-[C(Ar)[double bond, length as m-dash]CH(Ar)-o-C2B10H7 in good to high yields. This protocol represents a new strategy for the catalytic selective polyfunctionalization of carboranes with different substituents.

Graphical abstract: Rhodium-catalyzed sequential B(3)-, B(4)-, and B(5)-trifunctionalization of o-carboranes with three different substituents

Supplementary files

Article information

Article type
Communication
Submitted
21 Okt. 2021
Accepted
07 Dec. 2021
First published
08 Dec. 2021

Chem. Commun., 2022,58, 629-632

Rhodium-catalyzed sequential B(3)-, B(4)-, and B(5)-trifunctionalization of o-carboranes with three different substituents

B. Cheng, Y. Chen, P. Zhou and Z. Xie, Chem. Commun., 2022, 58, 629 DOI: 10.1039/D1CC05936J

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