Enabling the Use of Alkyl Thianthrenium Salts in Cross‐Coupling Reactions by Copper Catalysis. (26th August 2021)

• Record Type: Journal Article
• Authors: Chen, Cheng; Wang, Minyan; Lu, Hongjian; Zhao, Binlin; Shi, Zhuangzhi
• Is Part Of: Angewandte Chemie. Volume 133:Number 40(2021)
• Page Start: 21924
• Page End: 21928
• Publication Date: 2021-08-26
• Subjects: alkynylation -- copper -- photoredox reactions -- radical -- sulfonium salts; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.202109723
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: Alkyl groups are one of the most widely used groups in organic synthesis. Here, a a series of thianthrenium salts have been synthesized that act as reliable alkylation reagents and readily engage in copper‐catalyzed Sonogashira reactions to build C(sp 3 )−C(sp) bonds under mild photochemical conditions. Diverse alkyl thianthrenium salts, including methyl and disubstituted thianthrenium salts, are employed with great functional breadth, since sensitive Cl, Br, and I atoms, which are poorly tolerated in conventional approaches, are compatible. The generality of the developed alkyl reagents has also been demonstrated in copper‐catalyzed Kumada reactions. Abstract : A series of thianthrenium salts have been developed that can undergo C(sp 3 )−S bond cleavage and be used as reliable alkyl reagents. This ability has been demonstrated in copper‐catalyzed Sonogashira and Kumada cross‐coupling reactions under mild conditions.