An Approach to One‐Pot Regioselective Synthesis of Indenones through Palladium‐Catalyzed Annulation in Water. Issue 30 (26th July 2018)

• Record Type: Journal Article
• Authors: Ramesh, Karu; Satyanarayana, Gedu
• Is Part Of: European journal of organic chemistry. Issue 30(2018)
• Page Start: 4135
• Page End: 4146
• Publication Date: 2018-07-26
• Subjects: Pd catalysis -- Domino reactions -- Indenones -- Annulation -- Neolignans -- Water chemistry -- Green chemistry; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201800591
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : A one‐pot synthesis of indenones is presented. The process involves palladium‐catalyzed annulation of ortho ‐halobenzaldehydes with internal alkynes. Notably, it proceeded successfully in water as the sole, and green, solvent. Significantly, unlike in earlier reports, this protocol showed excellent regioselectivity with unsymmetrical alkylarylacetylenes. Further, the strategy was extended to a one‐pot synthesis of a neolignan natural product. Abstract : Functionalized indenones have been synthesized through domino Pd‐catalyzed annulation of ortho ‐halobenzaldehydes with internal alkynes with use of water as sole, and green, solvent. This protocol showed excellent regioselectivity with unsymmetrical alkylarylacetylenes and the strategy was extended to the synthesis of a neolignan natural product.