异吲哚酮通过铜催化的分子内苄基 C-H 磺酰胺化反应合成。
Isoindolinones via Copper-Catalyzed Intramolecular Benzylic C-H Sulfamidation.
机构信息
School of Chemistry, University of Bristol , Bristol BS8 1TS, U.K.
出版信息
J Org Chem. 2017 Feb 3;82(3):1719-1725. doi: 10.1021/acs.joc.6b02970. Epub 2017 Jan 25.
PMID:28084074
Abstract
2-Benzyl-N-tosylbenzamides and related substrates undergo copper-catalyzed intramolecular sulfamidation at the benzylic methylene to give N-arylsuflonyl-1-arylisoindolinones, which can be N-deprotected using samarium iodide to generate the free 1-arylisoindolinones. Preliminary mechanistic studies indicate that the rate-determining step is not C-H bond cleavage but are instead consistent with slow oxidation of a copper π-arene intermediate.
摘要
2-苄基-N-对甲苯磺酰苯甲酰胺及相关底物在铜催化下于苄基亚甲基发生分子内磺酰胺化反应，生成 N-芳基磺酰基-1-芳基异吲哚啉酮，后者可用碘化钐脱保护基生成游离的 1-芳基异吲哚啉酮。初步的机理研究表明，速率决定步骤不是 C-H 键的断裂，而是与铜-π-芳基配合物中间体的缓慢氧化一致。
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