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.

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通过未活化烯烃的加氢烷基化合成季碳中心的方法：二十年的进展

烯烃双键功能化已被确立为构建精细分子的极好策略。特别是，烯烃的加氢烷基化代表了合成新的 C(sp ³ )–C(sp ³) 键，同时形成具有挑战性的四元碳中心。在过去的 20 年中，出现了许多探索烯烃双键不同反应模式的加氢烷基化方法。这篇综述介绍了烯烃与亲电过渡金属配合物配位时作为亲电伙伴的例子，或者在最近的方法中，当在金属氢化物氢原子转移反应中用作亲核自由基物种的前体时。这种独特的反应性，加上烯烃作为起始材料的广泛可用性以及在构建全碳 C(sp ³ ) 季中心方面的成功报道，使加氢烷基化反应成为合成具有增加分子复杂性的分子的理想平台。