title: Metal-Free Difunctionalization of Alkynes with 2-Chlorodithiane for Synthesis of β-Ketodithianes.
abstract: Dithianes are versatile umpolung intermediates in organic synthesis but have rarely been employed in radical cross-coupling reactions. Here we describe the oxidative coupling method for alkyne difunctionalization under metal-catalyst-free conditions. The efficient protocol directly affords a variety of β-ketodithianes in good to excellent yields with high regioselectivities. It provides a general pathway for accessing valuable dithianes with controlled formation of a new C-C bond and a C-O bond via a radical coupling pathway.
authors.affiliation: †School of Pharmacy and ‡State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, People's Republic of China.
authors.forename: Junshan
authors.initials: J
authors.lastname: Lai
authors.affiliation: †School of Pharmacy and ‡State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, People's Republic of China.
authors.forename: Lixia
authors.initials: L
authors.lastname: Tian
authors.affiliation: †School of Pharmacy and ‡State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, People's Republic of China.
authors.forename: Xing
authors.initials: X
authors.lastname: Huo
authors.affiliation: †School of Pharmacy and ‡State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, People's Republic of China.
authors.forename: Yuan
authors.initials: Y
authors.lastname: Zhang
authors.affiliation: †School of Pharmacy and ‡State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, People's Republic of China.
authors.forename: Xingang
authors.initials: X
authors.lastname: Xie
authors.affiliation: †School of Pharmacy and ‡State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, People's Republic of China.
authors.forename: Shouchu
authors.initials: S
authors.lastname: Tang
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D008670:Metals / Q000737:chemistry*; D015394:Molecular Structure; D058451:Oxidative Coupling; D011807:Quinolizines / Q000138:chemical synthesis* / Q000737:chemistry*; D013457:Sulfur Compounds / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: C000605071:2-chlorodithiane; D000480:Alkynes; D007659:Ketones; D008670:Metals; D011807:Quinolizines; D013457:Sulfur Compounds; C438055:dithiane