Palladium-catalyzed Cs2CO3-promoted arylation of unactivated C(sp(3))-H bonds by (diacetoxyiodo)arenes: shifting the reactivity of (diacetoxyiodo)arenes from acetoxylation to arylation

The Journal of Organic Chemistry
Quan GouJun Qin

Abstract

PdCl2(CH3CN)2-catalyzed arylation of unactivated C(sp(3))-H bonds using (diacetoxyiodo)arenes as arylation reagents is reported. The reactivity of (diacetoxyiodo)arenes as arylation reagents is enabled in the presence of Cs2CO3 under the reaction conditions. This arylation method is highly efficient and occurs without the use of silver salt. The reaction tolerates a broad substrate scope that was not demonstrated by other silver salt-free C(sp(3))-H bond arylation conditions. The synthetic utility of the method is further illustrated in the synthesis of the psychotropic drug phenibut. A detailed mechanism study has been conducted to understand the reaction pathway.

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Citations

Jun 9, 2016·The Journal of Organic Chemistry·Ganesh PandeyDeepak Singh
Aug 6, 2015·Dalton Transactions : an International Journal of Inorganic Chemistry·Vinod G LandgeEkambaram Balaraman
Jul 24, 2018·Chemical Society Reviews·Carlo SambiagioMichael Schnürch
Sep 12, 2015·Chemistry : a European Journal·Quan GouJun Qin
Feb 10, 2021·Chemistry : a European Journal·Liam S Fitzgerald, Miriam L O'Duill
Feb 23, 2019·The Journal of Organic Chemistry·Li ChengTuan-Jie Li
Jul 13, 2017·Chemical Reviews·Jian HeJin-Quan Yu

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