4148-81-6Relevant articles and documents
Chemoselective Homologation-Deoxygenation Strategy Enabling the Direct Conversion of Carbonyls into (n+1)-Halomethyl-Alkanes
Citarella, Andrea,Holzer, Wolfgang,Ielo, Laura,Langer, Thierry,Miele, Margherita,Pace, Vittorio,Urban, Ernst,Zehl, Martin
supporting information, p. 7629 - 7634 (2020/10/12)
The sequential installation of a carbenoid and a hydride into a carbonyl, furnishing halomethyl alkyl derivatives, is reported. Despite the employment of carbenoids as nucleophiles in reactions with carbon-centered electrophiles, sp3-type alkyl halides remain elusive materials for selective one-carbon homologations. Our tactic levers on using carbonyls as starting materials and enables uniformly high yields and chemocontrol. The tactic is flexible and is not limited to carbenoids. Also, diverse carbanion-like species can act as nucleophiles, thus making it of general applicability.
Hydrothiolation of Alkenes and Alkynes Catalyzed by 3,4-Dimethyl-5-vinylthiazolium iodide and Poly(3,4-dimethyl-5-vinylthiazolium) iodide
Chun, Supill,Chung, Junyong,Park, Ji Eun,Chung, Young Keun
, p. 2476 - 2481 (2016/08/24)
The highly selective anti-Markovnikov addition of thiols to unactivated alkenes and alkynes was demonstrated by using 3,4-dimethyl-5-vinylthiazolium iodide or its polymer, poly(3,4-dimethyl-5-vinylthiazolium) iodide, as a complementary catalyst. The reaction proceeded cleanly under base-free conditions in air with both aromatic and aliphatic thiols. The polymer catalyst showed a high turnover number (≈5800) and could be reused up to four times without any loss of catalytic activity. DFT calculations supported stabilization of the thiyl radical intermediate by the thiazolium cation, which resulted in reaction of the radical with unsaturated C?C bonds.
Nickel-catalyzed alkenylative cross-coupling reaction of alkyl sulfides
Ishizuka, Kentaro,Seike, Hirofumi,Hatakeyama, Takuji,Nakamura, Masaharu
supporting information; experimental part, p. 13117 - 13119 (2010/11/05)
A novel cross-coupling reaction of alkyl aryl sulfides with aryl Grignard reagents has been achieved to produce the alkenyl-aryl coupling products in high yields by using catalytic Ni(cod)2 and a bulky N-heterocyclic carbene ligand, SIPr.