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Nickel-Catalyzed Reductive Deoxygenation of Diverse C–O Bond-Bearing Functional Groups
ACS Catalysis ( IF 11.3 ) Pub Date : 2021-10-19 , DOI: 10.1021/acscatal.1c03980 Adam Cook 1 , Haydn MacLean 1 , Piers St. Onge 1 , Stephen G. Newman 1
ACS Catalysis ( IF 11.3 ) Pub Date : 2021-10-19 , DOI: 10.1021/acscatal.1c03980 Adam Cook 1 , Haydn MacLean 1 , Piers St. Onge 1 , Stephen G. Newman 1
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We report a catalytic method for the direct deoxygenation of various C–O bond-containing functional groups. Using a Ni(II) pre-catalyst and silane reducing agent, alcohols, epoxides, and ethers are reduced to the corresponding alkane. Unsaturated species including aldehydes and ketones are also deoxygenated via initial formation of an intermediate silylated alcohol. The reaction is chemoselective for C(sp3)–O bonds, leaving amines, anilines, aryl ethers, alkenes, and nitrogen-containing heterocycles untouched. Applications toward catalytic deuteration, benzyl ether deprotection, and the valorization of biomass-derived feedstocks demonstrate some of the practical aspects of this methodology.
中文翻译：
镍催化的不同碳氧键官能团的还原脱氧
我们报告了一种用于各种含 C-O 键官能团的直接脱氧的催化方法。使用 Ni(II) 预催化剂和硅烷还原剂，醇、环氧化物和醚被还原为相应的烷烃。包括醛和酮在内的不饱和物质也通过中间体甲硅烷基化醇的初始形成而脱氧。该反应对 C(sp 3 )-O 键具有化学选择性，而胺、苯胺、芳基醚、烯烃和含氮杂环不受影响。催化氘化、苄醚脱保护和生物质衍生原料的价值化的应用证明了该方法的一些实际方面。
更新日期：2021-11-05
中文翻译：
镍催化的不同碳氧键官能团的还原脱氧
我们报告了一种用于各种含 C-O 键官能团的直接脱氧的催化方法。使用 Ni(II) 预催化剂和硅烷还原剂，醇、环氧化物和醚被还原为相应的烷烃。包括醛和酮在内的不饱和物质也通过中间体甲硅烷基化醇的初始形成而脱氧。该反应对 C(sp 3 )-O 键具有化学选择性，而胺、苯胺、芳基醚、烯烃和含氮杂环不受影响。催化氘化、苄醚脱保护和生物质衍生原料的价值化的应用证明了该方法的一些实际方面。
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