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Nickel‐Catalyzed 1,2‐Diarylation of Alkenyl Carboxylates: A Gateway to 1,2,3‐Trifunctionalized Building Blocks
Author(s) -
Derosa Joseph,
Kang Taeho,
Tran Van T.,
Wisniewski Steven R.,
Karunananda Malkanthi K.,
Jankins Tanner C.,
Xu Kane L.,
Engle Keary M.
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201913062
Subject(s) - alkene , catalysis , chemistry , aryl , yield (engineering) , nickel , stereocenter , combinatorial chemistry , carboxylate , organic chemistry , enantioselective synthesis , materials science , alkyl , metallurgy
A nickel‐catalyzed conjunctive cross‐coupling of alkenyl carboxylic acids, aryl iodides, and aryl/alkenyl boronic esters is reported. The reaction delivers the desired 1,2‐diarylated and 1,2‐arylalkenylated products with excellent regiocontrol. To demonstrate the synthetic utility of the method, a representative product is prepared on gram scale and then diversified to eight 1,2,3‐trifunctionalized building blocks using two‐electron and one‐electron logic. Using this method, three routes toward bioactive molecules are improved in terms of yield and/or step count. This method represents the first example of catalytic 1,2‐diarylation of an alkene directed by a native carboxylate group.