Synthesis of C-1 Deuterated 3-Formylindoles by Organophotoredox Catalyzed Direct Formylation of Indoles with Deuterated Glyoxylic Acid

• DOI: 10.1021/acs.orglett.2c01768
• Publication Date: 2022-07-08T03:52:41Z
• Authors: Yue Dong; Xiangmin Li; Peng Ji; Feng Gao; Xiang Meng; Wei Wang
• Keywords: Isatin; Indoles; Glyoxylates; Oxidants; 01 natural sciences; Catalysis; 0104 chemical sciences

Direct formylation of feedstock indoles with newly developed, cost-effective deuterated glyoxylic acid as formylation agent under visible light and air (O2) as terminal oxidant has been developed. An isatin byproduct produced from the corresponding indole reactant serves as a facilitator for the formylation process. The simple, mild, metal- and oxidant-free protocol enables the synthesis of structurally diverse C1-deuterated 3-formylindoles with broad functional group tolerance and late-stage functionalization at a high level of D-incorporation (95-99%).