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

Beilstein Journal of Organic Chemistry

Thiago S. Silva¹  Fernando Coelho¹ 

[1] Laboratory of Synthesis of Natural Products and Drugs, Department of Organic Chemistry, Chemistry Institute, University of Campinas, PO Box 6154 - 13083-970, Campinas – SP, Brazil;

关键词: hydroalkylation;    hydrogen atom transfer;    quaternary carbon center;    radical addition;    unactivated olefins;   

DOI  :  10.3762/bjoc.17.112

来源: DOAJ

【 摘 要 】

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(sp3)–C(sp3) 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(sp3) quaternary centers, makes hydroalkylation reactions an ideal platform for the synthesis of molecules with increased molecular complexity.

【 授权许可】

Unknown