Rhodium(III)‐Catalyzed Cross‐Coupling of Sulfoxonium Ylides with Quinoline‐8‐carboxaldehydes for Synthesis of Quinoline‐1, 3‐diketones. Issue 1 (26th November 2020)

• Record Type: Journal Article
• Authors: Lyu, Xue‐Li; Huang, Shi‐Sheng; Huang, Yuan‐Qiong; Song, Hong‐Jian; Liu, Yu‐Xiu; Li, Yong‐Qiang; Yang, Shao‐Xiang; Wang, Qing‐Min
• Is Part Of: Asian journal of organic chemistry. Volume 10:Issue 1(2021)
• Page Start: 176
• Page End: 179
• Publication Date: 2020-11-26
• Subjects: Rhodium(III)-catalysis -- Quinoline-8-carboxaldehyde -- Sulfoxonium ylides -- Acylmethylation -- Quinoline-1, 3-diketones; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.202000581
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: Herein, we report a protocol for rhodium(III)‐catalyzed aldehydic C(sp 2 )−H acylmethylation reactions of quinoline‐8‐carboxaldehydes using sulfoxonium ylides as carbene precursors to afford 1, 3‐diketones, which readily tautomerized to their enol forms. We determined the reaction mechanism by synthesizing the key intermediate, a five‐membered‐ring acylrhodium species. Abstract : A protocol for Rh(III)‐ catalyzed direct cross‐coupling reactions between sulfoxonium ylides and the C(sp 2 )−H bonds of quinoline‐8‐carboxaldehydes to smoothly afford the corresponding 1, 3‐diketones under redox‐neutral conditions was described. Owing to conjugation and hydrogen bonding, the enol forms of the products are more stable than the diketone forms. And the protocol has a broad substrate scope and high functional group tolerance.