Electrocatalytic three-component annulation-halosulfonylation of 1,6-enynes toward 1-indanones using sodium halides as both halogen sources and electrolytes

• Published in: Green chemistry : an international journal and green chemistry resource : GC Vol. 22; no. 13; pp. 4259 - 4269
• Main Authors: Zhang, Tian-Shu, Hao, Wen-Juan, Wang, Rong, Wang, Shi-Chao, Tu, Shu-Jiang, Jiang, Bo
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 06.07.2020; Royal Society of Chemistry
• Subjects: Additives; Catalysts; catalytic activity; Chemical reactions; Chemistry; Chemistry, Multidisciplinary; Crystallography; Electrochemistry; Electrolytes; Green & Sustainable Science & Technology; Green chemistry; Halides; halogens; Organic chemistry; Oxidants; Oxidizing agents; Physical Sciences; Reagents; Salts; Science & Technology; Science & Technology - Other Topics; sodium; Sodium halides; stereoselective synthesis; Stereoselectivity; Substrates; Transition metals; METAL-FREE SYNTHESIS; H FUNCTIONALIZATION; PALLADIUM; ASYMMETRIC-SYNTHESIS; SULFONYL IODIDES; QUINONE METHIDES; STEREOSELECTIVE-SYNTHESIS; ORGANIC ELECTROSYNTHESIS; CYCLIZATION; ACCESS
• ISSN: 1463-9262; 1463-9270; 1463-9270
• DOI: 10.1039/d0gc00771d

A new electrochemically induced three-component annulation-halosulfonylation of 1,6-enynes has been developed for stereoselective synthesis of 33 examples of 1-indanones with generally good yields under environmentally benign conditions. This electrochemical strategy can proceed in a simple undivided cell, avoiding any transition metal catalysts, chemical oxidants and additives. This reaction tolerates a wide scope of substrates, which provides a new and green access to fabricate important bioactive 1-indanone scaffolds. Notably, readily available and low-cost halogen salts play triple roles of an electrolyte and a redox catalyst as well as a halogenating reagent. A new electrochemically induced three-component annulation-halosulfonylation of 1,6-enynes has been developed for stereoselective synthesis of 33 examples of 1-indanones with generally good yields under environmentally benign conditions.