Rhodium(III)‐Catalyzed Cascade C−H Coupling/C‐Terminus Michael Addition of N‐Phenoxy Amides with 1, 6‐Enynes. Issue 25 (1st July 2021)

• Record Type: Journal Article
• Authors: Wei, Yinhui; Jiang, Xinlin; Gao, Hui; Bian, Mengyao; Huang, Yugang; Zhou, Zhi; Yi, Wei
• Is Part Of: ChemistrySelect. Volume 6:Issue 25(2021)
• Page Start: 6574
• Page End: 6578
• Publication Date: 2021-07-01
• Subjects: C−H Activation -- Derivatization -- Enynes -- N-Phenoxy amides -- Rhodium(III) catalyst; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.202102186
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: Described herein is a Rh(III)‐catalyzed regio‐/stereoselective C−H coupling/C‐terminus Michael addition cascade of N ‐phenoxy amides with 1, 6‐enynes, giving access to bicyclic frameworks with the retention of the oxidizing directing groups. Thus, it also provides a straightforward platform for subsequent derivatization via two‐fold C−H functionalization. Mechanistic studies elucidate the tandem reaction path and the coordination effect in tuning the observed manifold. Abstract : Herein, a Rh(III)‐catalyzed regio‐/stereoselective C−H coupling/C‐terminus Michael addition cascade of N ‐phenoxy amides with 1, 6‐enynes has been realized to give the bicyclic frameworks with good substrate/functional group tolerance and the retention of the oxidizing directing groups, thereby providing a straightforward platform for subsequent derivatization via two‐fold C−H functionalization. Mechanistic studies suggested that the coordination effect of the rhodium metal center with the oxygen atom and the ketene moiety played a crucial role in determining the reaction outcome.