Copper‐Catalyzed Trifunctionalization of Alkynes: Rapid Formation of Oxindoles Bearing Geminal Diboronates. Issue 4 (13th December 2018)

• Record Type: Journal Article
• Authors: He, Tao; Li, Bin; Liu, Li‐Chuan; Wang, Jing; Ma, Wen‐Peng; Li, Guang‐Yu; Zhang, Qing‐Wei; He, Wei
• Is Part Of: Chemistry. Volume 25:Issue 4(2019)
• Page Start: 966
• Page End: 970
• Publication Date: 2018-12-13
• Subjects: alkynes -- bis-borylation -- copper -- oxindoles -- trifunctionalization; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201804480
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: A copper‐catalyzed trifunctionalization of alkynes that provides rapid access to oxindoles bearing a geminal diboronate side chain, highlighted by the simultaneous formation of one C−C bond and two C−B bonds, is reported. This new reaction features simple reaction conditions (ligand‐free catalysis), a general substrate scope, and excellent chemoselectivity. Mechanistic study revealed a reaction sequence constituted by, in the order, borylation, intramolecular cross‐coupling, hydroboration, which has been rarely documented. Abstract : A ligand‐free Cu I ‐catalyzed trifunctionalization of 2‐ynamide was developed, which provides rapid access to oxindoles bearing a geminal diboronate substitution on the side chain. The new reaction features simple reaction conditions, a general substrate scope and excellent chemoselectivity.