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Issue 98, 2019
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Completely regioselective insertion of unsymmetrical alkynes into electron-deficient alkenes for the synthesis of new pentacyclic indoles

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Abstract

A Lewis acid-catalyzed insertion of unsymmetrical alkynes into electron-deficient alkenes was developed for the first time, and used to produce 34 hitherto unreported pentacyclic benzo[5,6]chromeno[2,3-b]indoles with generally good yields and complete stereoselectivity. A Yb(OTf)3-catalyzed reaction between o-alkynylnaphthols and 3-methyleneindolin-2-ones proceeded efficiently, and provided a simple and convergent protocol for alkyne difunctionalization via oxidant-free C–C double bond breaking/rearrangement. Mechanistic details of this domino process were derived by conducting systematic theoretical calculations.

Graphical abstract: Completely regioselective insertion of unsymmetrical alkynes into electron-deficient alkenes for the synthesis of new pentacyclic indoles

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Article information


Submitted
09 Nov 2019
Accepted
18 Nov 2019
First published
18 Nov 2019

Chem. Commun., 2019,55, 14757-14760
Article type
Communication

Completely regioselective insertion of unsymmetrical alkynes into electron-deficient alkenes for the synthesis of new pentacyclic indoles

K. Chen, T. Xu, J. Liang, M. Zhou, J. Zhang, W. Hao, J. Wang, S. Tu and B. Jiang, Chem. Commun., 2019, 55, 14757
DOI: 10.1039/C9CC08762A

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