Transition-metal-free cross-coupling reaction of iodocarboranes with terminal alkynes enabled by UV light : Synthesis of 1-alkynyl-o-carboranes and carborane-fused cyclics

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journalpeer-review

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Author(s)

Detail(s)

Original languageEnglish
Pages (from-to)18661-18667
Journal / PublicationJournal of the American Chemical Society
Volume142
Issue number43
Online published13 Oct 2020
Publication statusPublished - 28 Oct 2020
Externally publishedYes

Abstract

A transition-metal-free coupling protocol between iodocarboranes and terminal alkynes enabled by light at room temperature has been developed, leading to the synthesis of a variety of 1-alkynyl-o-carboranes. Moreover, following this strategy, the introduction of 1-I-3-aryl-o-carboranes or 1-I-2-aryl-o-carboranes results in the formation of o-carborane-fused cyclics. Interestingly, when 1-I-3- (p-R-C6H4)-o-carboranes are chosen as coupling partners, unexpected Rgroup migration products are also isolated. On the basis of the results of control experiments and isolation of the key intermediates, a possible reaction mechanism is then proposed, involving the formation of spiro radical species.

Citation Format(s)

Transition-metal-free cross-coupling reaction of iodocarboranes with terminal alkynes enabled by UV light : Synthesis of 1-alkynyl-o-carboranes and carborane-fused cyclics. / Ni, Hangcheng; Lu, Zhenpin; Xie, Zuowei.

In: Journal of the American Chemical Society, Vol. 142, No. 43, 28.10.2020, p. 18661-18667.

Research output: Journal Publications and Reviews (RGC: 21, 22, 62)21_Publication in refereed journalpeer-review