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

Isatin Indoles Glyoxylates Oxidants 01 natural sciences Catalysis 0104 chemical sciences
DOI: 10.1021/acs.orglett.2c01768 Publication Date: 2022-07-08T03:52:41Z
ABSTRACT
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%).
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