The catalytic, undirected borylation of alkyl C–H bonds typically occurs at high reaction temperatures or with excess substrate, or both, because of the low reactivity of alkyl C–H bonds. Here we report a new iridium system comprising 2-anilino-1,10-phenanthroline as ligand that catalyzes the borylation of alkyl C–H bonds with little to no induction period and with high reaction rates. This superior activation and reactivity profile of 2-aminophenanthroline catalysts leads to broader scope of the reaction, including those with sensitive reactants, such as epoxides and glycosidic acetals, enhanced diastereoselectivity, and higher yields of borylated products. These catalysts also enable the borylation of alkanes, amines, and ethers at room temperature for the first time. Mechanistic studies imply that facile N-borylation occurs under the reaction conditions, and that iridium complexes containing N-boryl aminophenanthrolines are competent precatalysts for the reaction.

中文翻译：

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2-氨基菲咯啉可实现烷基 C-H 键的温和、非定向硼化

由于烷基 C-H 键的反应活性较低，烷基 C-H 键的催化、非定向硼基化通常发生在高反应温度或过量底物或两者兼而有之的情况下。在这里，我们报道了一种新的铱系统，包含 2-苯胺基-1,10-菲咯啉作为配体，催化烷基 C-H 键的硼基化，几乎没有诱导期，反应速率高。2-氨基菲咯啉催化剂的这种优异的活化和反应性特征导致反应范围更广，包括那些具有敏感反应物（例如环氧化物和糖苷缩醛）的反应，增强的非对映选择性和更高的硼化产物产率。这些催化剂还首次实现了烷烃、胺和醚在室温下的硼基化。机理研究表明，在反应条件下容易发生 N-硼基化，并且含有 N-硼基氨基菲咯啉的铱配合物是该反应的有效预催化剂。