{"title":"Photo-Induced Difluoroethylation or Monofluoromethyl Sulfonylation of 2-Amino Aryl Ethynes to Access Diverse Seven-Membered N-Heterocycles","authors":"Yunfei Tian, Luping Zheng, Dongyu Guo, Xinping Ding, Weijun Fu, Zejiang Li","doi":"10.1002/ejoc.202400969","DOIUrl":null,"url":null,"abstract":"A photo-induced two/three-component radical difluoroethylation or monofluoromethyl sulfonylation of 2-amino aryl ethynes was smoothly finished, which gave a series of difluoroethyl or monofluoromethyl sulfonyl seven-membered N-heterocycles. The two radical systems featured simple/mild reaction conditions, good substrate scopes, and excellent E/Z selectivity. In addition, various radical intermediates were successfully detected by HRMS to explore the reaction process. Single-crystal X-ray diffraction and scaled-up experiments examined the product scaffold and application of this cyclization system.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"9 1","pages":""},"PeriodicalIF":2.5000,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"European Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/ejoc.202400969","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
A photo-induced two/three-component radical difluoroethylation or monofluoromethyl sulfonylation of 2-amino aryl ethynes was smoothly finished, which gave a series of difluoroethyl or monofluoromethyl sulfonyl seven-membered N-heterocycles. The two radical systems featured simple/mild reaction conditions, good substrate scopes, and excellent E/Z selectivity. In addition, various radical intermediates were successfully detected by HRMS to explore the reaction process. Single-crystal X-ray diffraction and scaled-up experiments examined the product scaffold and application of this cyclization system.
期刊介绍:
The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies.
The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry:
Liebigs Annalen
Bulletin des Sociétés Chimiques Belges
Bulletin de la Société Chimique de France
Gazzetta Chimica Italiana
Recueil des Travaux Chimiques des Pays-Bas
Anales de Química
Chimika Chronika
Revista Portuguesa de Química
ACH—Models in Chemistry
Polish Journal of Chemistry.