Dutta Subhabrata, Erchinger Johannes E, Schäfers Felix, Das Ankita, Daniliuc Constantin G, Glorius Frank
Westfälische Wilhelms-Universität Münster, Organisch-Chemisches Institut, Corrensstraße 36, 48149, Münster, Germany.
Angew Chem Int Ed Engl. 2022 Dec 5;61(49):e202212136. doi: 10.1002/anie.202212136. Epub 2022 Nov 9.
Herein, a Cr/Photoredox-catalyzed general synthetic strategy to access α-benzylic alcohols, isochromanones, oxy alcohols and thio alcohols is unveiled. Alkylation of aldehydes being a crucial C-C bond forming reaction, designing competent catalytic systems would render an attractive and decorated set of diverse alcohol motifs. Considering the challenges associated with classical organometallic chemistry, the strategy of dual catalysis is applied here to generate diverse alcohol motifs in a mild and efficient manner. The amalgamation of photocatalysis with chromium chemistry is chosen for this purpose to generate an environment with low basicity and thus, high chemoselectivity. With alkyl silanes as preferred coupling partners, this catalytic setup produces a broad substrate scope with an excellent functional group tolerance and displays a facile scale-up as well. Its application towards biologically relevant molecules and product diversification contributes to the synthetic utility of this method.
在此，一种用于合成α-苄醇、异色满酮、羟基醇和硫醇的Cr/光氧化还原催化通用合成策略被揭示。醛的烷基化作为一种关键的碳-碳键形成反应，设计有效的催化体系将产生一组有吸引力且多样的醇类结构单元。考虑到传统有机金属化学所面临的挑战，这里应用双催化策略以温和且高效的方式生成多样的醇类结构单元。为此选择光催化与铬化学的结合，以产生低碱度环境，从而具有高化学选择性。以烷基硅烷作为优选的偶联伙伴，这种催化体系具有广泛的底物范围、出色的官能团耐受性，并且易于放大。其在生物相关分子及产物多样化方面的应用提升了该方法的合成效用。
