A ligand-controlled switch of regioselectivity in ring-opening coupling of diarylmethylenecyclopropa[b]naphthalenes with Grignard reagents. Issue 2 (18th November 2015)

• Record Type: Journal Article
• Authors: Cao, Jian; Huang, Xian; Wu, Luling
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 2(2016)
• Page Start: 729
• Page End: 737
• Publication Date: 2015-11-18
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c3ob42084a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A ligand-controlled regioselectivity switch of ring-opening coupling reaction of diarylmethylenecyclopropa[ b ]naphthalenes with Grignard reagents providing differently substituted β-vinylic naphthalenes in moderate to excellent yields was reported. Based on careful NMR study, we concluded that it may be explained by the ligand effect. Abstract : A ligand-controlled regioselectivity switch of ring-opening coupling reaction of diarylmethylenecyclopropa[ b ]naphthalenes with Grignard reagents providing differently substituted β-vinylic naphthalenes in moderate to excellent yields was reported: when Pd(OAc)2 was used, the aromatic group from the Grignard reagent regioselectively coupled to the naphthyl ring after the ring-opening of three-membered cycle, which is different from the Pd(PPh3 )2 Cl2 -catalyzed reaction. Based on a careful NMR study, we concluded that it may be explained by the ligand effect.