Issue 14, 2022
From the journal:

Chemical Science

Thioether-enabled palladium-catalyzed atroposelective C–H olefination for N–C and C–C axial chirality†

Yanjun Li,‡a   Yan-Cheng Liou,‡a   Xinran Chen‡ab  and  Lutz Ackermann ORCID logo *a  

* Corresponding authors

a Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstraße 2, 37077 Göttingen, Germany
E-mail: Lutz.Ackermann@chemie.uni-goettingen.de

b Department of Chemistry, Zhejiang University Hangzhou, China

Abstract

Thioethers allowed for highly atroposelective C–H olefinations by a palladium/chiral phosphoric acid catalytic system under ambient air. Both N–C and C–C axial chiral (hetero)biaryls were successfully constructed, leading to a broad range of axially chiral N-aryl indoles and biaryls with excellent enantioselectivities up to 99% ee. Experimental and computational studies were conducted to unravel the walking mode for the atroposelective C–H olefination. A plausible chiral induction model for the enantioselectivity-determining step was established by detailed DFT calculations.

Graphical abstract: Thioether-enabled palladium-catalyzed atroposelective C–H olefination for N–C and C–C axial chirality

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Article information

DOI
https://doi.org/10.1039/D2SC00748G
Article type
Edge Article
Submitted
04 Feb 2022
Accepted
10 Mar 2022
First published
10 Mar 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2022,13, 4088-4094

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Thioether-enabled palladium-catalyzed atroposelective C–H olefination for N–C and C–C axial chirality

Y. Li, Y. Liou, X. Chen and L. Ackermann, Chem. Sci., 2022, 13, 4088 DOI: 10.1039/D2SC00748G

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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