Chemo‐ and Regioselective Catalyst‐Controlled Carbocyclization of Alkynyl Ketones: Rapid Synthesis of 1‐Indanones and 1‐Naphthols. Issue 32 (10th May 2019)

• Record Type: Journal Article
• Authors: Song, Liangliang; Tian, Guilong; Van der Eycken, Erik V.
• Is Part Of: Chemistry. Volume 25:Issue 32(2019)
• Page Start: 7645
• Page End: 7648
• Publication Date: 2019-05-10
• Subjects: carbocyclizations -- C−H activation -- copper -- enolates -- rhodium; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201901860
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: A catalyst‐controlled intramolecular carbocyclization of 2‐alkynyl aryl ketones is presented. Under rhodium(III) catalysis, 1‐indanones are formed through 5‐ exo ‐ dig carbocyclizations with exclusive chemo‐, regio‐ and stereoselectivity. When catalyzed by copper(I), 1‐naphthols are obtained through 6‐ endo ‐ dig carbocyclizations with exclusive chemo‐ and regioselectivity. Abstract : Indeed, the catalyst matters : A catalyst‐controlled 5‐ exo ‐ dig and 6‐ endo ‐ dig carbocyclization of 2‐alkynyl aryl ketones for the rapid synthesis of 1‐indanones and 1‐naphthols with exclusive chemo‐, regioselectivity is reported.