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Stereoselective Rhodium-Catalyzed 2-C-H 1,3-Dienylation of In-doles-Dual Functions of the Directing Group

Abstract

A rhodium-catalyzed intermolecular highly stereoselective 1,3-dienylation at the 2-position of indoles with non-terminal allenyl carbonates has been developed by using 2-pyrimidinyl or pyridinyl as the directing group. The reaction tolerates many functional groups affording the products in decent yields under mild conditions. In addition to the C-H bond activation, the directing group also played a vital role in determination of Z-stereoselectivity for the C-H functionalization reaction with 4-aryl-2,3-allenyl carbonates, which is confirmed by the E-selectivity observed with 4-alkyl-2,3-allenyl carbonates. DFT calculation has been conducted to reveal that π-π stacking involving the directing 2-pyrimidinyl or pyridinyl group is the origin of the observed stereoselectivity. Various synthetic transformations have also been demonstrate.

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Article information


Submitted
19 Apr 2021
Accepted
16 Jul 2021
First published
21 Jul 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

Stereoselective Rhodium-Catalyzed 2-C-H 1,3-Dienylation of In-doles-Dual Functions of the Directing Group

Y. Zhai, X. Zhang and S. Ma, Chem. Sci., 2021, Accepted Manuscript , DOI: 10.1039/D1SC02167B

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