Synthesis of β‐Phenylchalcogeno‐α,β‐unsaturated Ketones via Hydrochalcogenation of Acetylenes using Microwave and Solvent‐Free Conditions

References

• Comasseto , J. V. , Ling , L. W. , Petragnani , N. and Stefani , H. A. 1997 . Vinylic selenides and tellurides—preparation, reactivity and synthetic applications . Synthesis , : 373
   Google Scholar
• Petragnani , N. and Stefani , H. A. 2005 . Advances in organic tellurium chemistry . Tetrahedron , 61 : 1613
   Web of Science ®Google Scholar
• Comasseto , J. V. and Barrientos‐Astigarraga , R. E. 2000 . Add a little tellurium to your synthetic plans . Aldrich. Acta , 33 : 66
   Web of Science ®Google Scholar
• Harmata , M. and Jones , D. 1996 . Intramolecular 4+3 cycloadditions: Vinylthionium ions from allylic alcohols . Tetrahedron Lett. , 37 : 783
   Web of Science ®Google Scholar
• Trost , B. M. and Ornstein , P. L. 1981 . A chemoselective desulfurization method via homogeneous nickel catalysis . Tetrahedron Lett. , 22 : 3463
   Web of Science ®Google Scholar
• Wenkert , E. and Ferreira , T. W. 1982 . A general olefin synthesis . J. Chem. Soc., Chem. Commun. , : 840
   Google Scholar
• Bohlmann , F. and Bresinsky , E. 1964 . Polyacetylenic compounds, LX: Condensation of acetylenecarboxylic acid esters with mercaptans . Chem. Ber. , 97 : 2109
   Google Scholar
• Zhao , C.‐Q. , Huang , X. and Meng , J.‐B. 1998 . Stereo and regioselective synthesis of (Z)‐β‐arylseleno‐α,β‐unsaturated ketones via selenocarbonylation addition of arylselenoesters to alkynes catalyzed by copper(I) . Tetrahedron Lett. , 39 : 1933
   Google Scholar
• Barrientos‐Astigarraga , R. E. , Castelani , P. , Sumida , C. Y. and Comasseto , J. V. 1999 . Synthesis of functionalized tri‐ and tetrasubstituted vinylic tellurides from enolphosphates through vinylic substitution by lithium butyltellurolate . Tetrahedron Lett. , 40 : 7717
   Google Scholar
• Hamaguchi , M. and Nagai , T. 1989 . Strong participation of selenium substituents in decomposition of pyrazolines formed by 1,3‐dipolar cycloaddition of appropriate vinyl selenides with diazoalkanes . J. Org. Chem. , 54 : 3957
   Google Scholar
• Buzilova , S. R. , Sadekov , I. D. , Lipovich , T. V. , Fillipova , T. M. and Vereshchagin , L. I. 1977 . Nucleophilic addition of arenetellurollate and areneselenolate ions . J. Org. Chem. (USSR) , 47 : 1828
   Google Scholar
• Omar , M. T. and Basyouni , M. N. 1974 . Stereochemistry of ionic thiol addition to acetylenic ketones . Bull. Chem. Soc. Jpn. , 47 : 2325
   Web of Science ®Google Scholar
• Takehiko , N. and Yoshimore , O. 1981 . Reduction of β‐arylthio‐ or β‐alkylthio‐α,β‐unsaturated ketones . J. Chem. Soc., Perkin Trans. 1 , : 934
   Google Scholar
• Takehiko , N. and Yoshimore , O. 1979 . Reduction of β‐alkylthio α,β‐unsaturated ketones with lithium tetrahydroaluminate or sodium tetrahydroborate: conversion to α,β‐unsaturated ketones . Chem. Lett. , : 365
   Google Scholar
• Truce , W. E. and Goldhamer , D. L. 1959 . The stereochemistry of the base‐catalyzed addition of p‐toluenethiol to sodium and ethyl phenylpropiolate . J. Am. Chem. Soc. , 81 : 5795
   Google Scholar
• Detty , M. R. and Murray , B. J. 1983 . Cyclization of 3‐(arylchalcogeno)propenoyl chlorides, 2: Chalcogen and substituent control in the regiochemistry of intramolecular acylation: Preparation of benzo[b]telluropyrones . J. Am. Chem. Soc. , 105 : 883
   Web of Science ®Google Scholar
• Uemura , S. and Fukuzawa , S. 1982 . Ni(II)‐ and Co(II)‐phosphine complex catalyzed carbon–carbon bond formation between organic tellurides and grignard reagents . Tetrahedron Lett. , 23 : 1181
   Web of Science ®Google Scholar
• Braga , A. L. , Alves , E. F. , Silveira , C. C. and Andrade , L. H. 2000 . Stereoselective addition of sodium organyl chalcogenolates to alkynylphosphonates: synthesis of diethyl 2‐(organyl)‐2‐(organochalcogenyl)vinylphosphonates . Tetrahedron Lett. , 41 : 161
   Web of Science ®Google Scholar
• Dabdoub , M. J. , Baroni , A. C. M. , Lenardão , E. J. , Gianeti , T. R. and Hurtado , G. R. 2001 . Synthesis of (Z)‐1‐phenylseleno‐1,4‐diorganyl‐1‐buten‐3‐ynes: Hydroselenation of symmetrical and unsymmetrical 1,4‐diorganyl‐1,3‐butadiynes . Tetrahedron , 57 : 4271
   Web of Science ®Google Scholar
• Zeni , G. , Formiga , H. B. and Comasseto , J. V. 2000 . Improved procedure for the hydrotelluration of alkynes . Tetrahedron Lett. , 41 : 1311
   Web of Science ®Google Scholar
• Perin , G. , Jacob , R. G. , Botteselle , G. V. , Kublik , E. L. , Lenardão , E. J. , Cella , R. and Santos , P. C. S. 2005 . Clean and atom‐economic synthesis of α‐phenylselenoacrylonitiles and α‐phenylseleno‐α,β‐unsaturated esters by knoevenagel reaction under solvent‐free conditions . J. Braz. Chem. Soc. , 16 : 857
   Google Scholar
• Perin , G. , Jacob , R. G. , Azambuja , F. , Botteselle , G. V. , Siqueira , G. M. , Freitag , R. A. and Lenardão , E. J. 2005 . The first synthesis of β‐phenylchalcogeno‐α,β‐unsaturated esters via hydrochalcogenation of acetylenes using microwave and solvent‐free conditions . Tetrahedron Lett. , 46 : 1679
   Web of Science ®Google Scholar
• Jacob , R. G. , Perin , G. , Loi , L. N. , Pinno , C. S. and Lenardão , E. J. 2003 . Green synthesis of (−)‐isopulegol from (+)‐citonellal: Application to essential oil of citronella . Tetrahedron Lett. , 44 : 3605
   Web of Science ®Google Scholar
• Jacob , R. G. , Perin , G. , Botteselle , G. V. and Lenardão , E. J. 2003 . Clean and atom‐economic synthesis of octahydroacridines: Application to essential oil of citronella . Tetrahedron Lett. , 44 : 6809
   Google Scholar
• Varma , R. S. and Saini , R. K. 1997 . Microwave‐assisted reduction of carbonyl compounds in solid state using sodium borohydride supported on alumina . Tetrahedron Lett. , 38 : 4337
   Web of Science ®Google Scholar
• Kingston , H. M. 1988 . Introduction to Microwave Sample Preparation—Theory and Practice Washington, DC : American Chemical Society .
   Google Scholar