Thioamide-directed cobalt(III)-catalyzed selective amidation of C(sp3)@H bonds

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Thioamide-directed cobalt(III)-catalyzed selective amidation of C(sp3)@H bonds
Title:
Thioamide-directed cobalt(III)-catalyzed selective amidation of C(sp3)@H bonds
Other Titles:
Angewandte Chemie International Edition
Keywords:
Publication Date:
28 October 2017
Citation:
Tan, P. W.; Mak, A. M.; Sullivan, M. B.; Dixon, D. J.; Seayad, J., Thioamide-directed cobalt(III)-catalyzed selective amidation of C(sp3)@H bonds. Angewandte Chemie International Edition 2017, 56 (52), 16550-16554.
Abstract:
A mild, oxidant‐free, and selective Cp*CoIII‐catalyzed amidation of thioamides with robust dioxazolone amidating agents via C(sp3)−H bond activation to generate the desired amidated products is reported. The method is efficient and allows for the C−H amidation of a wide range of functionalized thioamides with aryl‐, heteroaryl‐, and alkyl‐substituted dioxazolones under the Cp*CoIII‐catalyzed conditions. The observed regioselectivity towards primary C(sp3)−H activation is supported by computational studies and the cyclometalation is proposed to proceed by means of an external carboxylate‐assisted concerted metalation/deprotonation mechanism. The reported method is a rare example of the use of a directing group other than the commonly used pyridine and quinolone classes for Cp*CoIII‐catalyzed C(sp3)−H functionalization and the first to exploit thioamides.
License type:
PublisherCopyrights
Funding Info:
Predoctoral fellowship by University of Oxford and the Agency for Science, Technology and Research (A*STAR) Singapore.
Description:
This is the peer reviewed version of the following article: Tan, P. W.; Mak, A. M.; Sullivan, M. B.; Dixon, D. J.; Seayad, J., Thioamide-directed cobalt(III)-catalyzed selective amidation of C(sp3)@H bonds. Angewandte Chemie International Edition 2017, 56 (52), 16550-16554, which has been published in final form at https://doi.org/10.1002/anie.201709273. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.
ISSN:
1433-7851
1521-3773
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