89005-19-6Relevant academic research and scientific papers
Redox-Neutral Arylations of Vinyl Cation Intermediates
Kaiser, Daniel,Veiros, Luis F.,Maulide, Nuno
supporting information, p. 64 - 77 (2017/01/14)
Herein we present a new unified concept for C?C bond formation under redox-neutral conditions. Our strategy hinges upon interception of a vinyl cation with a sulfoxide resulting in simultaneous C–C and C?O bond formation and arylation. A range of structurally diverse vinyl cations are generated in situ in the presence of a sulfoxide, resulting in hydrative arylation, direct arylation of enol triflates and interrupted Meyer–Schuster rearrangement. Mechanistic investigations showcase the crucial role played by the fleeting vinyl cation intermediate and structural features that lead to its stabilization. Applications of the reaction products to synthesis are also presented. (Figure presented.).
A General and highly efficient protocol for the synthesis of chalcogenoacetylenes by copper(I)-terpyridine catalyst
Movassagh, Barahman,Yousefi, Ali,Momeni, Badri Zaman,Heydari, Sepideh
, p. 1385 - 1390 (2014/06/23)
A highly efficient copper-catalyzed Csp-X (X = S, Se, Te) bond-forming reaction of terminal alkynes and diorganyl dichalcogenides has been developed. This transformation was realized through the use of copper(I) iodide as a catalyst, 4′-(4-meth
Highly regioselective hydrosilylation of unsymmetric alkynes using a phenylthio directing group
Huang, Kuan-Hsun,Isobe, Minoru
supporting information, p. 4733 - 4740 (2014/08/05)
Cobalt-assisted hydrosilylation of acetylenes is particularly interesting in organic synthesis since alkynyl group functionalization can give way to more useful substructures. This study aims to answer the general question of how to control hydrosilylatio
Nickel-palladium-catalyzed hydroamination/cyclization of sulfur-substituted 1,6-diynes with secondary amines
Nagata, Hayami,Sugimoto, Yuko,Ito, Yukiteru,Tanaka, Miki,Yoshimatsu, Mitsuhiro
, p. 1306 - 1316 (2014/02/14)
Hydroamination/cyclizations of sulfur-substituted 1,6-diynes catalyzed by nickel or nickel-palladium in DMSO were examined. Pyrroles 2a-l and furans 5a-i bearing various secondary amines were obtained in high yields. The organosulfanylmethyl group on pyrr
Short and efficient preparation of alkynyl selenides, sulfides and tellurides from terminal alkynes
Bieber, Lothar W.,Da Silva, Margarete F.,Menezes, Paulo H.
, p. 2735 - 2737 (2007/10/03)
Diphenyl diselenide reacts with terminal alkynes at room temperature in DMSO in the presence of catalytic amounts of copper iodide to give good to excellent yields of alkynyl phenyl selenides. The reaction occurs under neutral conditions and the solvent a
An efficient and general synthesis of alkynyl sulfoxides
Kabanyane, Sidima T.,MaGee, David I.
, p. 2758 - 2763 (2007/10/02)
A convenient one-step method for the preparation of alkynyl phenyl sulfides using diphenyl disulfide has been developed.The oxidation of the corresponding sulfides to the sulfoxides, and not sulfones, was achieved by using trans-(phenylsulfonyl)-3-phenyloxaziridine.A variety of other oxidizing reagents was also investigated.
Stereoselective construction and synthetic applications of phenylthio substituted iodoolefins
Magriotis,Doyle,Kim
, p. 2541 - 2544 (2007/10/02)
(E)- and (Z)-Phenylthio substituted iodoolefins 1 and 2 have been synthesized stereoselectively via lower order stannylcuprate addition to and hydroalumination of appropriate alkyne precursors. Their utility in model studies on the synthesis of calichemic
Chemistry of Allene Sulphoxides: Novel Transformations of Acetylenic Alcohols
Cutting, Ian,Parsons, Philip J.
, p. 1209 - 1210 (2007/10/02)
The preparation and reactions of allenes derived from 1-phenylthio substituted acetylenic alcohols are described; this chemistry offers new routes to allenyl sulphides, acyl anion equivalents, and substituted unsaturated aldehydes.
