Design of an Indolylphosphine Ligand for Reductive Elimination-Demanding Monoarylation of Acetone Using Aryl Chlorides

Organic Letters
Wai Chung FuFuk Yee Kwong

Abstract

The rational design of a phosphine ligand for the reductive elimination-demanding Pd-catalyzed mono-α-arylation of acetone is demonstrated and reported. The catalyst is tolerant of previously proven challenging electron-deficient aryl chlorides and provides excellent product yields with down to 0.1 mol % Pd. Preliminary investigations suggest that the rate-limiting step for the proposed system is the oxidative addition of aryl chlorides, in which it contradicts previous findings regarding the α-arylation of acetone with aryl halides.

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Citations

Oct 21, 2015·The Journal of Organic Chemistry·Qingjing YangFuk Yee Kwong
May 26, 2017·The Journal of Organic Chemistry·Jindian Duan, Fuk Yee Kwong
Jan 4, 2017·Chemical Communications : Chem Comm·Yong WuAiwen Lei
May 5, 2018·Chemistry : a European Journal·Paola CaramentiJerome Waser
May 12, 2018·Chemistry, an Asian Journal·Chun-Hai Wang, Shang-Dong Yang
Oct 5, 2018·Organic & Biomolecular Chemistry·Long Chen, Yun-Xiang Zou
Jul 16, 2020·Angewandte Chemie·Sary Abou DerhamineAbderrahmane Amgoune

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