Grover Jagrit, Dutta Bishal, Ghosh Devika, Shee Prakash K, Maiti Siddhartha, Werz Daniel B, Maiti Debabrata
Department of Chemistry, IIT Bombay Powai Mumbai 400076 India
Logic Technology development, Intel Corporation Hillsboro Oregon 97124 USA.
Chem Sci. 2025 May 7;16(23):10141-10158. doi: 10.1039/d5sc00449g. eCollection 2025 Jun 11.
Transition metal catalyzed C-H functionalization has emerged as a robust tool in organic synthesis, as it utilizes the most abundant functional group of an organic compound, C-H bonds, omitting the need for pre-functionalization. Selectively functionalizing a particular C-H bond out of numerous C-H bonds present in the molecular skeleton is a fascinating and difficult task to perform. To differentiate between almost identical C-H bonds, various strategies have evolved. Directing group (DG) assistance, non-directed functionalizations, and non-covalent interactions have significantly contributed to addressing the challenge of regioselectivity in targeting distinct C-H bonds. However, further advancements are still required. Among various C-H functionalizations, C-H acetoxylation is a pivotal organic transformation which enables direct functionalization of otherwise inert C-H bonds into versatile acetoxy groups. In this review, various strategies for C-H acetoxylation, directed and non-directed C-H acetoxylation, electrochemical C-H acetoxylation, and photo-induced C-H acetoxylation, are covered. A comprehensive coverage provided by this review will be extremely useful to chemists in both academia and industry, who are striving to incorporate oxygen into organic molecular skeletons.
过渡金属催化的C-H官能团化已成为有机合成中一种强大的工具,因为它利用了有机化合物中最丰富的官能团——C-H键,无需预官能团化。从分子骨架中众多的C-H键中选择性地官能团化特定的C-H键是一项既迷人又艰巨的任务。为了区分几乎相同的C-H键,已经发展出了各种策略。导向基团(DG)辅助、非导向官能团化以及非共价相互作用在解决靶向不同C-H键时的区域选择性挑战方面做出了重大贡献。然而,仍需要进一步的进展。在各种C-H官能团化反应中,C-H乙酰氧基化是一种关键的有机转化反应,它能够将原本惰性的C-H键直接官能团化为多功能的乙酰氧基。在这篇综述中,涵盖了C-H乙酰氧基化的各种策略,包括导向和非导向的C-H乙酰氧基化、电化学C-H乙酰氧基化以及光诱导C-H乙酰氧基化。这篇综述提供的全面内容对于学术界和工业界中致力于将氧引入有机分子骨架的化学家来说将极为有用。