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Tandem [4 + 2]/[2 + 2] Cycloaddition of o-Carboryne with Enynes: Facile Construction of Carborane-fused Tricyclics

Abstract

o-Carboryne (1,2-dehydro-o-carborane) is a very useful synthon for the synthesis of a variety of carborane functionalized molecules. With 1-Li-2-OTf-o-C2B10H10 as precursor, o-carboryne undergoes an efficient [4 + 2] cycloaddition with various conjugated enynes, followed by a subsequent [2 + 2] cycloaddition at room temperature, generating a series of carborane-fused tricyclo[6.4.0.02,7]dodeca-2,12-dienes in moderate to high isolated yields. This reaction is compatible with many functional groups and has a broad substrate scope. A reactive carborane-fused 1,2-cyclohexadiene intermediate is involved, which is supported by experimental results and DFT calculations. This protocol offers a convenient strategy for the construction of complex carborane-functionalized tricyclics.

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Article information


Submitted
28 Dec 2020
Accepted
19 Feb 2021
First published
22 Feb 2021

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2021, Accepted Manuscript
Article type
Edge Article

Tandem [4 + 2]/[2 + 2] Cycloaddition of o-Carboryne with Enynes: Facile Construction of Carborane-fused Tricyclics

J. Zhang and Z. Xie, Chem. Sci., 2021, Accepted Manuscript , DOI: 10.1039/D0SC07047E

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