Abstract
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.
Highlights
Natural product structures remain some of the main sources of inspiration for the synthesis of new bioactive compounds [1,2]
A careful view of the carbon backbone of these natural molecules reveals their high molecular complexity [3,4,5], which can be described by the presence of multiple stereogenic centers in the same molecule, a substantial fraction of sp3 hybridized carbons (Fsp3) [6], and the presence of all-carbon quaternary centers (Figure 1)
The all-carbon quaternary center motif represents a challenge in modern organic synthesis due to the inherent steric issues associated with the formation of these particular C(sp3)–C(sp3) bonds [7,8,9,10,11,12,13]
Summary
Natural product structures remain some of the main sources of inspiration for the synthesis of new bioactive compounds [1,2]. A careful view of the carbon backbone of these natural molecules reveals their high molecular complexity [3,4,5], which can be described by the presence of multiple stereogenic centers in the same molecule, a substantial fraction of sp hybridized carbons (Fsp3) [6], and the presence of all-carbon quaternary centers (Figure 1). The all-carbon quaternary center motif represents a challenge in modern organic synthesis due to the inherent steric issues associated with the formation of these particular C(sp3)–C(sp3) bonds [7,8,9,10,11,12,13].
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