Kumar Sanjeev, Borkar Vaishnavi, Nunewar Saiprasad, Yadav Shashank, Kanchupalli Vinaykumar
Department of Process Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Hyderabad, 500 037, Telangana, India.
Chem Asian J. 2023 Apr 17;18(8):e202201201. doi: 10.1002/asia.202201201. Epub 2023 Mar 20.
An effective redox-neutral strategy to synthesize aryl/alkynyl and alkyl/alkynyl substituted 1-naphthol derivatives has been efficaciously developed by Rh(III)-catalyzed [4+2]-annulation of sulfoxonium ylides and 1,3-diynes with excellent regio- and chemoselectivity. Subsequently, the same strategy was extended to furnish various unsymmetrical binaphthol motifs in one-pot manner. Interestingly, the TMS-derived 1,3-diyne predominantly delivered the 3-alkynyl-1-naphthol via desilylation pathway. The salient features such as traceless directing group, broad substrate scope, good functional group tolerance, and operationally simple conditions made the present protocol more valuable and appealing.
通过铑（III）催化的氧化锍叶立德与1,3-二炔的[4+2]环化反应，以优异的区域和化学选择性，有效开发了一种合成芳基/炔基和烷基/炔基取代的1-萘酚衍生物的有效氧化还原中性策略。随后，相同的策略被扩展以一锅法提供各种不对称的联萘酚基序。有趣的是，TMS衍生的1,3-二炔主要通过去硅基化途径生成3-炔基-1-萘酚。无痕导向基团、广泛的底物范围、良好的官能团耐受性和操作简单的条件等显著特点使得本方法更具价值和吸引力。
