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[(PPh)NiCl] 催化的借氢策略 C-N 键形成反应:多样性仲胺和喹啉的合成。

[(PPh)NiCl]-Catalyzed C-N Bond Formation Reaction via Borrowing Hydrogen Strategy: Access to Diverse Secondary Amines and Quinolines.

机构信息

Department of Chemistry, Indian Institute of Technology Madras, Chennai 600036, India.

出版信息

J Org Chem. 2021 May 7;86(9):6994-7001. doi: 10.1021/acs.joc.1c00510. Epub 2021 Apr 27.

Abstract

Commercially available [(PPh)NiCl] was found to be an efficient catalyst for the mono--alkylation of (hetero)aromatic amines, employing alcohols to deliver diverse secondary amines, including the drug intermediates chloropyramine () and mepyramine (), in excellent yields (up to 97%) via the borrowing hydrogen strategy. This method shows a superior activity (TON up to 10000) with a broad substrate scope at a low catalyst loading of 1 mol % and a short reaction time. Further, this strategy is also successful in accessing various quinoline derivatives following the acceptorless dehydrogenation pathway.

摘要

市售的[(PPh)NiCl]被发现是一种高效的催化剂,可用于(杂)芳胺的单烷化反应,通过 borrowing hydrogen 策略,醇可作为氢源,将多种仲胺,包括药物中间体氯吡拉敏()和甲吡拉敏(),高效地转化为相应的产物,产率高达 97%。该方法在 1 mol%的低催化剂负载量和较短的反应时间下,具有优异的活性(TON 高达 10000)和广泛的底物范围。此外,该策略还可成功应用于无受体脱氢途径,得到各种喹啉衍生物。

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