Department of Chemistry, Birla Institute of Technology and Science, Pilani (BITS Pilani), Hyderabad Campus, Jawahar Nagar, Hyderabad 500078 Telangana, India.
J Org Chem. 2021 Jun 4;86(11):7881-7890. doi: 10.1021/acs.joc.1c00861. Epub 2021 May 24.
An iodine-catalyzed sustainable, cost-effective, and atom-economic synthetic methodology is developed to synthesize a wide variety of valuable sulfenylphenanthrenes and polycyclic heteroaromatics in moderate to high yield through electrophilic thiolative annulation of 2-alkynyl biaryls (6- cyclization) using methyl sulfoxides such as dimethyl sulfoxide (DMSO) as the sulfur source under transition-metal-free conditions. The transformation requires only iodine in a catalytic amount and trifluoroacetic anhydride. Notably, DMSO played multiple roles such as methylthiolating reagent, oxidant, and solvent in this reaction.
发展了一种碘催化的可持续、经济高效、原子经济性的合成方法，通过使用二甲亚砜（DMSO）等甲基亚砜作为硫源，在无过渡金属条件下，使 2-炔基联苯（6-环化）进行亲电硫叶立德环化，以中等至高产率合成了各种有价值的亚磺酰基菲和多环杂芳烃。该转化仅需催化量的碘和三氟乙酸酐。值得注意的是，DMSO 在该反应中起到了多种作用，如甲基硫代试剂、氧化剂和溶剂。
