Cardiff Catalysis Institute, School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, CF10 3AT, UK.
Chem Soc Rev. 2021 Mar 21;50(6):3720-3737. doi: 10.1039/d0cs00531b. Epub 2021 Feb 3.
The manipulation of amino C-H bonds has garnered significant interest from the synthetic community due to its inherently high atom, step and redox economy. This Tutorial Review summarises the ability of boranes to mediate hydride abstraction from α-amino and γ-amino conjugated C-H bonds. Borane-mediated hydride abstraction results in the generation of reactive iminium hydridoborate salts that participate in a variety of stoichiometric and catalytic processes. The reactions that have utilised this unusual reactivity include those that manipulate amino scaffolds (including dehydrogenation, racemisation, isomerisation, α- and β-functionalisation, and C-N bond cleavage) and those that use amine-based reagents (transfer hydrogenation, and alkylation).
由于其固有的高原子经济性、高步骤经济性和高氧化还原经济性，氨基酸 C-H 键的操控引起了合成界的极大兴趣。本综述总结了硼烷介导的从α-氨基和γ-氨基共轭 C-H 键中脱去氢的能力。硼烷介导的氢化物抽提导致生成反应性亚胺氢硼酸盐盐，其参与各种计量和催化过程。利用这种不寻常的反应性的反应包括那些操纵氨基酸支架的反应（包括脱氢、外消旋化、异构化、α-和β-官能化以及 C-N 键断裂）和那些使用基于胺的试剂的反应（转移氢化和烷基化）。
