Methodologies for the synthesis of quaternary carbon centers via hydroalkylation of unactivated olefins: twenty years of advances

Autor(es)

Silva, Thiago S. ^[1] ; Coelho, Fernando ^[1]

Afiliação do(s) autor(es)

^[1] Univ Estadual Campinas, Lab Synth Nat Prod & Drugs, Dept Organ Chem, Inst Chem, POB 6154, BR-13083970 Campinas, SP - Brazil

• Tipo de documento: Artigo de Revisão
• Fonte: Beilstein Journal of Organic Chemistry; v. 17, p. 1565-1590, JUL 7 2021.
• Citações Web of Science: 0

Resumo

Olefin double-bond functionalization has been established as an excellent strategy for the construction of elaborate molecules. In particular, the hydroalkylation of olefins represents a straightforward strategy for the synthesis of new C(sp(3))-C(sp(3)) bonds, with concomitant formation of challenging quaternary carbon centers. In the last 20 years, numerous hydroalkylation methodologies have emerged that have explored the diverse reactivity patterns of the olefin double bond. This review presents examples of olefins acting as electrophilic partners when coordinated with electrophilic transition-metal complexes or, in more recent approaches, when used as precursors of nucleophilic radical species in metal hydride hydrogen atom transfer reactions. This unique reactivity, combined with the wide availability of olefins as starting materials and the success reported in the construction of all-carbon C(sp(3)) quaternary centers, makes hydroalkylation reactions an ideal platform for the synthesis of molecules with increased molecular complexity. (AU)

• Processo FAPESP: 13/07600-3 - CIBFar - Centro de Inovação em Biodiversidade e Fármacos
• Beneficiário: Glaucius Oliva
• Modalidade de apoio: Auxílio à Pesquisa - Centros de Pesquisa, Inovação e Difusão - CEPIDs
• Processo FAPESP: 18/02611-0 - A pós-Funcionalização de Pequenas Moléculas Poli-funcionalizadas: Uma Abordagem Robusta para a Síntese de Novos Padrões Estruturais com Potencial Atividade Biológica
• Beneficiário: Fernando Antonio Santos Coelho
• Modalidade de apoio: Auxílio à Pesquisa - Regular