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
15 ربيع الأول 1443
Accepted
03 جمادى الأولى 1443
First published
04 جمادى الأولى 1443

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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