18277-20-8Relevant articles and documents
C?C Bond Formation of Benzyl Alcohols and Alkynes Using a Catalytic Amount of KOtBu: Unusual Regioselectivity through a Radical Mechanism
Kumar, Amit,Janes, Trevor,Chakraborty, Subrata,Daw, Prosenjit,von Wolff, Niklas,Carmieli, Raanan,Diskin-Posner, Yael,Milstein, David
supporting information, p. 3373 - 3377 (2019/02/14)
We report a C?C bond-forming reaction between benzyl alcohols and alkynes in the presence of a catalytic amount of KOtBu to form α-alkylated ketones in which the C=O group is located on the side derived from the alcohol. The reaction proceeds under thermal conditions (125 °C) and produces no waste, making the reaction highly atom efficient, environmentally benign, and sustainable. Based on our mechanistic investigations, we propose that the reaction proceeds through radical pathways.
Room-Temperature Alkynylation of Phosphine Oxides with Copper Acetylides: Practical Synthesis of Alkynylphosphine Oxides
Gérard, Phidéline,Veillard, Romain,Alayrac, Carole,Gaumont, Annie-Claude,Evano, Gwilherm
, p. 633 - 638 (2017/01/18)
An efficient procedure for the synthesis of alkynylphosphine oxides based on the oxidative alkynylation of secondary phosphine oxides with copper acetylides was developed. Activation with molecular oxygen in the presence of either a mixture of 1,2-dimethylimidazole and triethylamine or N-methylimidazole alone enabled the formal umpolung of the poorly nucleophilic copper acetylides, which were coupled with phosphine oxides under remarkably mild conditions. Notable features of this procedure are the availability of the starting materials, its user-friendliness, and its mild conditions, which allow the synthesis of complex alkynylphosphine oxides.
Copper(II)-Promoted, One-Pot Conversion of 1-Alkynes with Anhydrides or Primary Amines to the Respective 2,5-Disubstituted Furans or Pyrroles under Microwave Irradiation Conditions
Lee, Hyejeong,Yi, Yeonhui,Jun, Chul-Ho
, p. 3485 - 3490 (2016/01/25)
Furans and pyrroles are prepared from 1-alkynes by using a Cu(II)-promoted, one-pot, microwave irradiation method. Glaser coupling of 1-alkynes and cyclization of the resulting 1,3-diyne in the presence of an anhydride or a primary amine results in the formation of the respective 2,5-diaryl- or 2,5-dialkyl-substituted furans and pyrroles.