Nickel‐Catalyzed 1, 2‐Diarylation of Alkenyl Carboxylates: A Gateway to 1, 2, 3‐Trifunctionalized Building Blocks. Issue 3 (12th December 2019)

• Record Type: Journal Article
• Authors: Derosa, Joseph; Kang, Taeho; Tran, Van T.; Wisniewski, Steven R.; Karunananda, Malkanthi K.; Jankins, Tanner C.; Xu, Kane L.; Engle, Keary M.
• Is Part Of: Angewandte Chemie international edition. Volume 59:Issue 3(2020)
• Page Start: 1201
• Page End: 1205
• Publication Date: 2019-12-12
• Subjects: carboxylic acid -- diarylation -- nickel -- trifunctionalization; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201913062
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: 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. Abstract : Easy as 1, 2, 3 : Under nickel catalysis, alkenyl carboxylic acids undergo selective 1, 2‐diarylation. The resulting products can then be readily converted into diverse 1, 2, 3‐trifunctionalized motifs via classical carboxylic acid interconversions and modern decarboxylative cross‐couplings.