Efficient Synthesis of Aryl Methyl Sulfide Derivatives Using (Methylthio)trimethylsilane as Methylthiolation Reagent

REFERENCES

• (a) The World Drug Index contains over 300 reports of aryl methyl sulfides and aryl methyl sulfones ; (b) Jarvest , R. L. ; Berge , J. M. ; Brown , M. J. ; Brown , P. ; Elder , J. S. ; Forrest , A. K. ; Houge-Frydrych , C. S. V. ; O'Hanlon , P. J. ; McNair , D. J. ; Rittenhouse , S. ; Sheppard , R. J. Optimisation of aryl substitution leading to potent methionyl tRNA synthetase inhibitors with excellent gram-Positive antibacterial activity . Bioorg. Med. Chem. Lett. 2003 , 13 , 665 – 668 ; (c) Conlon , D. A. ; Drahus-Paone , A. ; Ho , G.-J. ; Pipik , B. ; Helmy , R. ; McNamara , J. M. ; Shi , Y.-J. ; Williams , J. M. ; Macdonald , D. ; Deschênes , D. ; Gallant , M. ; Mastracchio , A. ; Roy , B. ; Scheigetz , J. Process Development and Large-Scale Synthesis of a PDE4 Inhibitor . Org. Process Res. Dev. 2006 , 10 , 36 – 45 ; (d) Lu , W. ; Chen , P. ; Lin , G. New stereoselective synthesis of thiamphenicol and florfenicol from enantiomerically pure cyanohydrin: A chemo-enzymatic approach . Tetrahedron 2008 , 64 , 7822 – 7827 ; (e) Caturla , F. ; Amat , M. ; Reinoso , R. F. ; Córdoba , M. ; Warrellow , G. Racemic and chiral sulfoxides as potential prodrugs of the COX-2 inhibitors Vioxx and Arcoxia . Bioorg. Med. Chem. Lett. 2006 , 16 , 3209 – 3212 ; (f) Morrow , R. J. ; Millership , J. S. ; Collier , P. S. Facile syntheses of the three major metabolites of thioridazine . Helv. Chim. Acta 2005 , 88 , 962 – 967 ; (g) Vernon , M. W. ; Heel , R. C. ; Brogden , R. N. Enoximone. A review of its pharmacological properties and therapeutic potential . Drugs 1991 , 42 , 997 – 1017 .
   PubMed Web of Science ®Google Scholar
• (a) Cremlyn , R. J. An Introduction to Organosulfur Chemistry ; Wiley : New York , 1996 ; (b) Seebach, D.; Neumann, H. Bromine-lithium exchange in vinyl and aryl bromides with tert-butylithium. Ring enlargement via dibromocarbene adducts. Chem. Ber., 1974, 107, 847–853; (c) Perlow, D. S.; Kuo, M. S. Moritz, H. M.; Wai, J. S. Egbertson, M.S. Practical synthesis of 4-fluoro-2-(methylthio)benzylamine and the corresponding sulfone and sulfonamide. Synth. Commun. 2007, 37, 1887–1897; (d) Ham, J.; Yang, I.; Kang, H. A facile one-pot synthesis of alkyl aryl sulfides from aryl bromides. J. Org. Chem. 2004, 69, 3236–3239 .
   Google Scholar
• (a) Migita , T. ; Shimizu , T. ; Asami , Y. ; Shiobara , J. ; Kato , Y. ; Kosugi , M. The palladium catalyzed nucleophilic substitution of aryl halides by thiolate anions . Bull. Chem. Soc. Jpn. 1980 , 53 , 1385 – 1389 ; (b) Kondo , T. ; Mitsudo , T. Metal-catalyzed carbon-sulfur bond formation . Chem. Rev. 2000 , 100 , 3205 – 3220 ; (c) Zheng , N. ; McWilliams , J. C. ; Fleitz , F. J. ; Armstrong III , J. D. ; Volante , R. P. Palladium-catalyzed synthesis of aryl sulfides from aryl triflates . J. Org. Chem. 1998 , 63 , 9606 – 9607 ; (d) Kwong , F. Y. ; Buchwald , S. L. A general, efficient, and inexpensive catalyst system for the coupling of aryl iodides and thiols . Org. Lett. 2002 , 4 , 3517 – 3520 ; (e) Itoh , T. ; Mase , T. A general palladium-catalyzed coupling of aryl bromides/triflates and thiols . Org. Lett. 2004 , 6 , 4587 – 4590 ; (f) Fernandez-Rodriguez , M. A. ; Shen , Q. ; Hartwig , J. F. A general and long-lived catalyst for the palladium-catalyzed coupling of aryl halides with thiols . J. Am. Chem. Soc. 2006 , 128 , 2180 – 2181 ; (g) Baskin , J. M. ; Wang , Z. An efficient copper catalyst for the formation of sulfones from sulfinic acid salts and aryl iodides . Org. Lett. 2002 , 4 , 4423 – 4425 .
   Web of Science ®Google Scholar
• (a) Montanari , S. ; Paradisi , C. ; Scorrano , G. Influence of ion pairing, steric effects, and other specific interactions on the reactivity of thioanions with chloronitrobenzenes. Nucleophilic aromatic substitution vs. reduction. J. Org. Chem. 1991, 56, 4274–4279; (b) Capkova , K. ; Yoneda , Y. ; Dickerson , T. J. ; Janda , K. D. Synthesis and structure-activity relationships of second-generation hydroxamate botulinum neurotoxin A protease inhibitors. Bioorg. Med. Chem. Lett. 2007, 17, 6463–6466; (c) Johnson , N. W. ; Semones , M. ; Adams , J. L. ; Hansbury , M. ; Winkler , J. Optimization of triarylimidazoles for Tie2: Influence of conformation on potency. Bioorg. Med. Chem. Lett. 2007, 17, 5514–5517.
   Web of Science ®Google Scholar
• Kondoh , A. ; Yorimitsu , H. ; Oshima , K. Nucleophilic aromatic substitution reaction of nitroarenes with alkyl- or arylthio groups in dimethyl sulfoxide by means of cesium carbonate . Tetrahedron 2006 , 62 , 2357 – 2360 .
   Web of Science ®Google Scholar
• Groutas , W. C. ; Felker , D. Synthetic applications of cyanotrimethylsilane, iodotrimethylsilane, azidotrimethylsilane, and methylthiotrimethylsilane . Synthesis. 1980 , 861 – 868 .
   Web of Science ®Google Scholar
• (a) Evans , D. A. ; Truesdale , L. K. ; Grimm , K. G. ; Nesbitt , S. L. Thiosilanes, a promising class of reagents for selective carbonyl protection . J. Am. Chem. Soc. 1977 , 99 , 5009 – 5017 ; (b) Mantus , E. K. ; Clardy , J. The synthesis of dithyreanitrile . Tetrahedron Lett. 1993 , 34 , 1085 – 1086 .
   Web of Science ®Google Scholar
• (a) Hanessian , S. ; Guindon , Y. Cleavage of methyl and benzyl ethers with thiotrimethylsilanes . Tetrahedron Lett. 1980 , 21 , 2305 – 2308 ; (b) Howell , G. P. ; Fletcher , S. P. ; Geurts , K. ; ter Horst , B. ; Feringa , B. L. Catalytic Asymmetric Synthesis of Acyclic Arrays by Tandem 1,4-Addition-Aldol Reactions . J. Am. Chem. Soc. 2006 , 128 , 14977 – 14985 ; (c) Kanemitsu , T. ; Wong , C.-H. ; Kanie , O. Solid-Phase Synthesis of Oligosaccharides and On-Resin Quantitative Monitoring Using Gated Decoupling 13C NMR . J. Am. Chem. Soc. 2002 , 124 , 3591 – 3599 .
   Web of Science ®Google Scholar
• Prakash , G. K. S. ; Hoole , D. ; Ha , D. S. Wilkinson , J. ; Olah , G. A. Convenient preparation of aryl methyl and aryl phenyl sulfides from arenediazonium tetrafluoroborates and trimethyl(methylthio)- and trimethyl(phenylthio)silanes . Arkivoc , 2002 , 13 , 50 – 54 .
   Google Scholar
• (a) Pang , Y.-P. ; Xu , K. ; Kollmeyer , T. M. ; Perola , E. ; McGrath , W. J. ; Green , D. T. ; Mangel , W. F. Discovery of a new inhibitor lead of adenovirus proteinase: Steps toward selective, irreversible inhibitors of cysteine proteinases . FEBS Lett. 2001 , 502 , 93 – 97 ; (b) Kornblum , N. ; Cheng , L. ; Kerber , R. C. ; Kestner , M. M. ; Newton , B. N. ; Pinnick , H. W. ; Smith , R. G. ; Wade , P. A. Displacement of the nitro group of substituted nitrobenzenes-a synthetically useful process . J. Org. Chem. 1976 , 41 , 1560 – 1564 ; (c) Beck , J. R. Nucleophilic displacement of aromatic nitro groups . Tetrahedron 1978 , 34 , 2057 – 2068 .
   PubMed Web of Science ®Google Scholar
• McBee , E. T. ; Graham , P. J. Alkylthio(trifluoromethyl)benzenes . J. Am. Chem. Soc. 1950 , 72 , 4235 – 4237 .
   Web of Science ®Google Scholar
• Pilgram , K. ; Korte , F. Thermolysis of O,O-dialkyl-S-arylthiophosphates . Tetrahedron 1965 , 21 , 1999 – 2013 .
   Web of Science ®Google Scholar
• Allaire , F. S. ; Lyga , J. W. Nonaqueous diazotization of arylamines in the presence of dimethyldisulfide; the convenient synthesis of arylmethylsulfides from anilines . Synth. Commun. 2001 , 1857 – 1861 .
   Web of Science ®Google Scholar