Beng Timothy K, Shearer Victoria, Davey Rachel, Redman Ivianne
Department of Chemistry, Central Washington University Ellensburg WA 98926 USA
RSC Adv. 2020 May 27;10(34):20264-20271. doi: 10.1039/d0ra03726e. eCollection 2020 May 26.
The C-H bond functionalization of sp carbon centres presents a significant challenge due to the inert nature of hydrocarbons as well as the need to selectively functionalize one of the numerous aliphatic C-H bonds embodied in organic molecules. Here, we describe catalytic, diastereoselective, and site-selective sp C-H hydroxylation/alkoxylation protocols featuring dihydroisoquinolones, γ-, and δ-lactams, which bear vicinal stereocenters. The hydroxylation strategy utilizes oxygen, a waste-free oxidant and affords attractive fragments for potential drug discovery. Fe-catalyzed dehydrative coupling of the resulting tertiary alcohols with simple primary alcohols has led to the construction of highly versatile unsymmetrical dialkyl ethers.
由于碳氢化合物的惰性本质以及需要选择性地官能团化有机分子中众多脂肪族碳氢键中的一个，sp碳中心的碳氢键官能团化面临着重大挑战。在此，我们描述了以二氢异喹啉酮、γ-和δ-内酰胺为特征的催化、非对映选择性和位点选择性的sp碳氢键羟基化/烷氧基化方案，这些化合物带有相邻的立体中心。羟基化策略利用氧气这种无废物氧化剂，并为潜在的药物发现提供了有吸引力的片段。铁催化所得叔醇与简单伯醇的脱水偶联反应已导致构建了高度通用的不对称二烷基醚。
