Synthesis of di(hetero)aryl sulfides by defluorinative sulfenylation of polyfluoroalkyl ketones with sodium sulfinates or arylsulfonyl chlorides

• Published in: Chemical communications (Cambridge, England) Vol. 56; no. 61; pp. 8699 - 872
• Main Authors: Chu, Xue-Qiang, Xie, Ting, Wang, Ya-Wen, Li, Xiang-Rui, Rao, Weidong, Xu, Haiyan, Shen, Zhi-Liang
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 07.08.2020; Royal Society of Chemistry
• Subjects: Aromatic compounds; chemical bonding; Chemical reactions; Chemistry; Chemistry, Multidisciplinary; Crystallography; Defluorination; heterocyclic compounds; Ketones; moieties; organic sulfur compounds; Perfluoroalkyl & polyfluoroalkyl substances; perfluorocarbons; Physical Sciences; Science & Technology; sodium; sulfides; sulfur; THIOLS; THIOLATION; C-S; SULFUR; BINDING; F BOND ACTIVATION; DISULFIDES
• ISSN: 1359-7345; 1364-548X; 1364-548X
• DOI: 10.1039/d0cc03303k

A facile incorporation of a privileged sulfide, a naphthofuran framework, and a perfluoroalkyl moiety in one molecule was successfully accomplished through tandem defluorinative sulfenylation of α-perfluoroalkyl ketones with a sulfur source. The reaction presumably proceeds via a sequence involving defluorination, reductive sulfenylation, autoaromatization, and annulation, accompanied by the simultaneous cleavage of four C(sp 3 )-F bonds and the formation of new C-S and C-O bonds. Cascade reactions of α-perfluoroalkyl ketones with sodium sulfinates or arylsulfonyl chlorides that allowed the efficient synthesis of fluoroalkylated di(hetero)aryl sulfide derivatives under transition metal-free conditions were developed.