Iridium-Catalyzed Enantioselective C(sp3)-H Borylation of Aminocyclopropanes was written by Shi, Yongjia;Yang, Yuhuan;Xu, Senmiao. And the article was included in Angewandte Chemie, International Edition in 2022.Formula: C8H13N This article mentions the following:
Transition-metal-catalyzed regio- and stereo-controllable C-H functionalization remains a formidable challenge in asym. catalysis. Herein, we disclose the first example of iridium-catalyzed C(sp3)-H borylation of aminocyclopropanes by using simple imides as weakly coordinating directing groups under mild reaction conditions. The reaction proceeded via a six-membered iridacycle, affording a vast range of chiral aminocyclopropyl boronates. The current method features a broad spectrum of functional groups (36 examples) and high enantioselectivities (up to 99%). We also demonstrated the synthetic utility by a preparative scale C-H borylation, C-B bond transformations, and conversion of the directing group. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Formula: C8H13N).
2-Cyclohexylacetonitrile (cas: 4435-14-7) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.Formula: C8H13N
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts