Visible light-induced carbonylation of indoles with arylsulfonyl chlorides and CO

• Published in: Tetrahedron Vol. 72; no. 51; pp. 8442 - 8448
• Main Authors: Li, Xiangguang, Liang, Deqiang, Huang, Wenzhong, Zhou, Hongfu, Li, Zhao, Wang, Baoling, Ma, Yinhai, Wang, Hai
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 22.12.2016; Elsevier
• Subjects: additives; ambient temperature; Arylsulfonyl chlorides; Carbonylation; catalysts; chemical reactions; chemical structure; Chemistry; Chemistry, Organic; chlorides; Indol-3-yl aryl ketones; Indoles; ketones; Physical Sciences; Science & Technology; Visible light photocatalysis; CNUDXZIIVQXZPC-UHFFFAOYSA-N; NVPXCWXWSBPXDF-UHFFFAOYSA-N; ZYKSGYYJRGISRP-UHFFFAOYSA-N; STRIBORQTQQOGQ-UHFFFAOYSA-N; KTTKHPWYMHHUNK-UHFFFAOYSA-N; GYHGHNRBULFTCV-UHFFFAOYSA-N; CWRCMJRJXRUQQY-UHFFFAOYSA-N; DEZXVNYMIKCZQE-UHFFFAOYSA-N; Indol-3-yl aryl ketones; XWRSPDBVPWWJRB-UHFFFAOYSA-N; OTPZEGYROFYGMD-UHFFFAOYSA-N; FHCSORPSRGLRSE-UHFFFAOYSA-N; OLYNNQUHOKOTNN-UHFFFAOYSA-N; MMCNUNMTVMSWGT-UHFFFAOYSA-N; Indoles; ZISFDOJYIBISAN-UHFFFAOYSA-N; Visible light photocatalysis; QEICLSLJPRCUOK-UHFFFAOYSA-N; HHONDBRSQQROHL-UHFFFAOYSA-N; Carbonylation; IOGFADXXFXBDIM-UHFFFAOYSA-N; Arylsulfonyl chlorides; KBCJZSDJMUWBFI-UHFFFAOYSA-N; QQJCFTFQXMLULS-UHFFFAOYSA-N; BXUARHYRLVXLKU-UHFFFAOYSA-N; ADHQLIGSIQGNBW-UHFFFAOYSA-N; ROUTE; ACYLATION; PHOTOREDOX CATALYSIS; KETONES; PALLADIUM-CATALYZED CARBONYLATION; ARYL; DERIVATIVES; EFFICIENT; METAL-FREE; ACCESS
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2016.11.009

A novel and simple strategy for the visible light-induced efficient synthesis of indol-3-yl aryl ketones from readily available arylsulfonyl chlorides and indoles with CO at room temperature was developed. This metal-free protocol has good functional group tolerance and avoids the use of transition-metal catalysts, additives, and alkaline or acidic reaction medium. [Display omitted]