Practical Ni-Catalyzed Aryl–Alkyl Cross-Coupling of Secondary Redox-Active Esters | Zendy

Josep Cornellà | Zendy; Jacob T. Edwards | Zendy; Tian Qin | Zendy; Shuhei Kawamura | Zendy; Jie Wang | Zendy; Chung-Mao Pan | Zendy; Ryan Gianatassio | Zendy; Michael A. Schmidt | Zendy; Martin D. Eastgate | Zendy; Phil S. Baran | Zendy

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Practical Ni-Catalyzed Aryl–Alkyl Cross-Coupling of Secondary Redox-Active Esters

Author(s) -

Josep Cornellà,

Jacob T. Edwards,

Tian Qin,

Shuhei Kawamura,

Jie Wang,

Chung-Mao Pan,

Ryan Gianatassio,

Michael A. Schmidt,

Martin D. Eastgate,

Phil S. Baran

Publication year - 2016

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/jacs.6b00250

Subject(s) - chemistry , alkyl , aryl , catalysis , reagent , halide , combinatorial chemistry , redox , coupling reaction , organic chemistry , substrate (aquarium) , oceanography , geology

A new transformation is presented that enables chemists to couple simple alkyl carboxylic acids with aryl zinc reagents under Ni-catalysis. The success of this reaction hinges on the unique use of redox-active esters that allow one to employ such derivatives as alkyl halides surrogates. The chemistry exhibits broad substrate scope and features a high degree of practicality. The simple procedure and extremely inexpensive nature of both the substrates and pre-catalyst (NiCl2·6H2O, ca. $9.5/mol) bode well for the immediate widespread adoption of this method.

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