Mondal Pinku Prasad, Das Subham, Venugopalan Sreelakshmi, Krishnan Malavika, Sahoo Basudev
School of Chemistry, Indian Institute of Science Education and Research Thiruvananthapuram, Thiruvananthapuram, 695551 Kerala, India.
Org Lett. 2023 Mar 10;25(9):1441-1446. doi: 10.1021/acs.orglett.3c00175. Epub 2023 Feb 23.
A visible-light-photocatalyzed 1,2-arylalkylation of -(arylsulfonyl)acrylamides with ketone-based dihydroquinazolinones is described. The formal C-C bond cleavage of aliphatic ketones is unified with tandem radical alkylation/1,4-aryl migration/desulfonylation to forge two different types of vicinal C-C bonds and construct an all-carbon quaternary α-stereocenter, thus enhancing the carbogenic complexity and tolerating diverse functionalities. Additional to telescopic synthesis and product diversification, this method features a radical dicarbofunctionalization of conjugated -(arylsulfonyl)acrylamides with a nucleophilic alkyl radical precursor (dihydroquinazolinone) utilizing oxygen as a green oxidant at ambient temperature.
本文描述了一种可见光光催化的基于酮的二氢喹唑啉酮与β-(芳基磺酰基)丙烯酰胺的1,2-芳基烷基化反应。脂肪族酮的形式C-C键断裂与串联自由基烷基化/1,4-芳基迁移/脱磺酰化反应相结合，形成两种不同类型的邻位C-C键，并构建一个全碳季碳α-立体中心，从而提高了碳源的复杂性并耐受多种官能团。除了可进行串联合成和产物多样化外，该方法还具有共轭β-(芳基磺酰基)丙烯酰胺与亲核烷基自由基前体（二氢喹唑啉酮）在室温下利用氧气作为绿色氧化剂进行自由基双碳官能化的特点。
