Nickel‐Catalyzed 1, 2‐Diarylation of Alkenyl Carboxylates: A Gateway to 1, 2, 3‐Trifunctionalized Building Blocks. (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. Volume 132:Number 3(2020)
• Page Start: 1217
• Page End: 1221
• Publication Date: 2019-12-12
• Subjects: Carbonsäuren -- Diarylierung -- Nickel -- Trifunktionalisierung; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201913062
• Languages: English
• ISSNs: 0044-8249

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 : Einfach wie 1, 2, 3 : Unter Nickelkatalyse werden Alkenylcarbonsäuren selektiv 1, 2‐diaryliert. Die dabei entstehenden Produkte können dann über klassische Carbonsäure‐Interkonversionen und moderne decarboxylierende Kreuzkupplungen problemlos in diverse 1, 2, 3‐trifunktionalisierte Motive umgewandelt werden.