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Allene C(sp(2))-H Activation and Alkenylation Catalyzed by Palladium

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Title
Allene C(sp(2))-H Activation and Alkenylation Catalyzed by Palladium
Author(s)
Schreib, Benedikt S.; Mina Son; Aouane, Francoise A.; Mu-Hyun Baik; Carreira, Erick M.
Publication Date
2021-12-29
Journal
Journal of the American Chemical Society, v.143, no.51, pp.21705 - 21712
Publisher
American Chemical Society
Abstract
The selective transition-metal-mediated activation of C(sp(2))-H bonds of allenes is a formidable challenge because of the competitive, intrinsic reactivity of cumulated double bonds. Herein, we report a Pd-catalyzed C-H alkenylation of electronically unbiased allenes, affording penta-1,2,4-triene products in up to 94% yield. A picolinamide directing group enables the formation of putative allenyl-palladacycles, which subsequently participate in a turnover-limiting Heck-type reaction with electron-deficient alkene coupling partners. This mechanistic proposal is consistent with experimental and computational investigations. Additionally, we report for the first time the use of picolinamide N,O-acetals as readily removable auxiliaries for C-H activation reactions, allowing the efficient alkenylation of allenyl carbinol derivatives. Successful removal of the directing groups without affecting the reactive penta-1,2,4-triene substructure of the products is demonstrated.
URI
https://pr.ibs.re.kr/handle/8788114/11028
DOI
10.1021/jacs.1c11528
ISSN
0002-7863
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > 1. Journal Papers (저널논문)
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