The transient-chelating-group-controlled stereoselective Rh(i)-catalyzed silylative aminocarbonylation of 2-alkynylanilines: access to (Z)-3-(silylmethylene)indolin-2-ones. Issue 32 (4th August 2022)

• Record Type: Journal Article
• Authors: Han, Ya-Fei; Lv, Gui-Fen; Li, Yang; Wu, Li-Jun; Ouyang, Xuan-Hui; Li, Jin-Heng
• Is Part Of: Chemical science. Volume 13:Issue 32(2022)
• Page Start: 9425
• Page End: 9431
• Publication Date: 2022-08-04
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d2sc03009h
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : Transient-chelating-group-controlled stereoselective rhodium(I)-catalyzed silylative aminocarbonylation of 2- alkynylanilines with CO and silanes toward (Z)-3-(silylmethylene)indolin-2-ones is presented. Abstract : A new method involving mild acryl transient-chelating-group-controlled stereoselective Rh(i )-catalyzed silylative aminocarbonylation of 2-alkynylanilines with CO and silanes is presented for producing ( Z )-3-(silylmethylene)indolin-2-ones. Upon using an acryl transient chelating group, 2-alkynylanilines undergo an unprecedented alkyne cis -silylrhodation followed by aminocarbonylation to assemble ( Z )-3-(silylmethylene)indolin-2-ones. Mechanistic studies show that acryl transient chelating effects result in the key alkyne cis -silylrhodation process.