Palladium-Catalyzed Electrophilic Functionalization of Pyridine Derivatives through Phosphonium Salts

Angewandte Chemie
Yuan-Yuan CheChao Feng

Abstract

Herein, we report a highly efficient and practical method for pyridine-derived heterobiaryls synthesis by resorting to palladium-catalyzed electrophilic functionalization of easily available pyridine-derived quaternary phosphonium salts. The nice generality of the present reaction protocol is further extrapolated beyond arylation regime by enabling facile incorporation of diverse carbon-based fragments, including alkenyl, alkynyl and also allyl, onto pyridine core. Notably, the silver salt additive is revealed to be of vital importance for the success of this transformation and its pivotal role as transmetallation mediator, which guarantees a smooth transfer of pyridyl group to palladium intermediate, is also disclosed.

References

Oct 3, 2002·Journal of the American Chemical Society·Brian D DangelDalibor Sames
Jun 25, 2004·Chemical Communications : Chem Comm·Yajun Wang, Frank Caruso
Oct 8, 2004·Journal of the American Chemical Society·Jacqueline E Milne, Stephen L Buchwald
Jan 21, 2006·Angewandte Chemie·Noriaki KudoGregory C Fu
Apr 28, 2006·Angewandte Chemie·Kelvin L BillingsleyStephen L Buchwald
Mar 6, 2007·Journal of the American Chemical Society·Ramesh GiriJin-Quan Yu
Sep 25, 2007·Journal of the American Chemical Society·Nadège BoudetPaul Knochel
Jul 12, 2008·Accounts of Chemical Research·Jared C LewisJonathan A Ellman
Jul 16, 2008·Accounts of Chemical Research·Ruben Martin, Stephen L Buchwald
Jan 19, 2010·Angewandte Chemie·Masayuki WasaJin-Quan Yu
Sep 4, 2010·Journal of the American Chemical Society·Ian B SeiplePhil S Baran
Sep 10, 2010·Chemistry : a European Journal·Matthew D Hill
Nov 26, 2010·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Seung-Hoi Kim, Reuben D Rieke
Apr 21, 2011·Journal of Medicinal Chemistry·Stephen D Roughley, Allan M Jordan
Apr 21, 2011·Chemistry : a European Journal·Dongbing ZhaoChangwei Hu
Nov 9, 2011·Journal of the American Chemical Society·Mengchun YeJin-Quan Yu
Nov 15, 2011·The Journal of Organic Chemistry·Ning Liu, Zhong-Xia Wang
Oct 11, 2014·Chemical Reviews·Christophe AllaisThierry Constantieux
Jan 30, 2016·Nature Communications·Zuyong DengJi-Chang Xiao
Feb 3, 2016·Organic Letters·Guo-Lin GaoJin-Quan Yu
Apr 28, 2016·Current Medicinal Chemistry·R ÁlvarezR Peláez
May 7, 2016·Current Topics in Medicinal Chemistry·Nisha DeviVirender Singh
Jun 4, 2016·The Journal of Organic Chemistry·Michael C D FürstMarkus R Heinrich
Oct 13, 2016·Journal of the American Chemical Society·Michael C HiltonAndrew McNally
Jun 25, 2017·Angewandte Chemie·Hai-Jun TangTeck-Peng Loh
Jan 30, 2018·Journal of the American Chemical Society·J Luke KoniarczykAndrew McNally
May 25, 2018·Journal of the American Chemical Society·Ryan D DolewskiAndrew McNally
Aug 8, 2018·Angewandte Chemie·Ryan G AndersonAndrew McNally
Aug 15, 2018·Angewandte Chemie·Gwilherm Evano, Cédric Theunissen

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Citations

Sep 18, 2020·Angewandte Chemie·Xinlan A F CookMichael C Willis
Jul 23, 2021·Organic Letters·Lukas V HoffKarl Gademann
Oct 20, 2021·Organic Letters·Huifei WangHongze Liang
Dec 18, 2021·Journal of the American Chemical Society·Kai KangDaniel J Weix

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