Chiral N,NLigands Enabling Palladium-Catalyzed Enantioselective Intramolecular Heck-Matsuda Carbonylation Reactions by Sequential Migratory and CO Insertions

Author(s)

Carmona, Rafaela C. ^[1] ; Koster, Otto D. ^[1] ; Duarte Correia, Carlos Roque ^[1]

Affiliation

^[1] Univ Estadual Campinas, Inst Chem, BR-10384612 Sao Paulo - Brazil

• Document type: Journal article
• Source: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION; v. 57, n. 37, p. 12067-12070, SEP 10 2018.
• Web of Science Citations: 19

Abstract

Unprecedented enantioselective intramolecular Heck carbonylation reactions of arenediazonium salts were enabled by a chiral N,Nligand. This reaction constitutes the first enantioselective Heck carbonylation that proceeds through migratory insertion followed by CO insertion. The enantioenriched functionalized dihydrobenzofurans were obtained in good to high yields and enantiomeric ratios of up to 98:2 under mild and operationally simple reaction conditions. (AU)

• FAPESP's process: 14/25770-6 - New frontiers in cross-coupling reactions promoted by palladium: combining enantioselective catalysis, C-H activations, new materials and in flux reactions aiming at high efficiency and sustainability in synthetic processes
• Grantee: Carlos Roque Duarte Correia
• Support Opportunities: Research Projects - Thematic Grants
• FAPESP's process: 18/00271-8 - Enantioselective Synthesis of Heterocylces via Intramolecular and Desymmetrizations Reacions Using Arenediazonium Salts
• Grantee: Rafaela Costa Carmona
• Support Opportunities: Scholarships in Brazil - Post-Doctoral
• FAPESP's process: 13/07600-3 - CIBFar - Center for Innovation in Biodiversity and Drug Discovery
• Grantee: Glaucius Oliva
• Support Opportunities: Research Grants - Research, Innovation and Dissemination Centers - RIDC
• FAPESP's process: 13/10183-5 - Arylation of Cycloalkenes via asymmetric Heck-Matsuda reaction and synthetic applications
• Grantee: Rafaela Costa Carmona
• Support Opportunities: Scholarships in Brazil - Doctorate