Nucleophilic arylation with tetraarylphosphonium salts

Nature Communications
Zuyong DengJi-Chang Xiao

Abstract

Organic phosphonium salts have served as important intermediates in synthetic chemistry. But the use of a substituent on the positive phosphorus as a nucleophile to construct C-C bond remains a significant challenge. Here we report an efficient transition-metal-free protocol for the direct nucleophilic arylation of carbonyls and imines with tetraarylphosphonium salts in the presence of caesium carbonate. The aryl nucleophile generated from phosphonium salt shows low basicity and good nucleophilicity, as evidenced by the successful conversion of enolizable aldehydes and ketones. The reaction is not particularly sensitive to water, shows wide substrate scope, and is compatible with a variety of functional groups including cyano and ester groups. Compared with the arylmetallic reagents that are usually moisture sensitive, the phosphonium salts are shelf-stable and can be easily handled.

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Citations

Jun 10, 2016·Organic Letters·Zuyong DengJi-Chang Xiao
Oct 13, 2016·Journal of the American Chemical Society·Michael C HiltonAndrew McNally
Jul 21, 2017·Organic Letters·Niklas B Heine, Armido Studer
Oct 7, 2016·Chemical Communications : Chem Comm·Shi-Meng WangCheng-Pan Zhang
Nov 11, 2017·Organic & Biomolecular Chemistry·Qingrui LiYangjie Wu
Jun 7, 2018·Chemical Communications : Chem Comm·Jia ChenJi-Chang Xiao
Jun 4, 2019·Molecular Diversity·Zain Maqsood CheemaAhmed Abbaskhan
Aug 26, 2020·Angewandte Chemie·Chris SlootwegBas de Bruin
Jul 25, 2019·Chemistry : a European Journal·Dmitry I BugaenkoAlexander V Karchava
Jun 21, 2017·Chemistry : a European Journal·Damian E YerienAl Postigo
May 19, 2018·Chemistry Central Journal·Humaira Yasmeen GondalM Iqbal Choudhary
Feb 23, 2019·Chemistry : a European Journal·Andrey BelyaevIgor O Koshevoy
Apr 8, 2020·Chemistry : a European Journal·Flip HoltropJ Chris Slootweg
May 14, 2021·Chemical Communications : Chem Comm·Vladimir O SmirnovAlexander D Dilman
Jun 22, 2021·Organic & Biomolecular Chemistry·Fabian SeifertIvan Vilotijevic
Jun 25, 2021·Angewandte Chemie·Robin WeissVictor Mamane
Jan 30, 2018·Journal of the American Chemical Society·J Luke KoniarczykAndrew McNally
Dec 7, 2018·Organic Letters·Liqi QiuFrancois Mathey
Dec 17, 2016·The Journal of Organic Chemistry·Zuyong DengJi-Chang Xiao
Aug 19, 2018·Journal of the American Chemical Society·Dipendu MandalRowan D Young
Aug 16, 2017·The Journal of Organic Chemistry·Elsa DeruerSylvain Canesi
Jan 15, 2020·Journal of the American Chemical Society·Dipendu MandalRowan D Young
May 10, 2018·Organic Letters·Jia ChenJi-Chang Xiao
Jul 11, 2018·The Journal of Organic Chemistry·Rahul N GaykarAkkattu T Biju
Feb 20, 2019·Inorganic Chemistry·Jean-Marc MörsdorfJoachim Ballmann
Aug 14, 2020·Accounts of Chemical Research·Jin-Hong Lin, Ji-Chang Xiao
Sep 4, 2021·The Journal of Organic Chemistry·Min ZhangJi-Chang Xiao
Oct 20, 2021·Organic Letters·Huifei WangHongze Liang

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Methods Mentioned

BETA
column chromatography

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