FeCl₃-Mediated Reaction of Alkynols with Iodine: An Efficient and Convenient Synthetic Route to Vinyl Iodides

REFERENCES

• For a recent reviews, see (a) Bolm , C. ; Legros , J. ; Paih , J. L. ; Zani , L. Iron-catalyzed reactions in organic synthesis . Chem. Rev. 2004 , 104 , 6217 – 6254 ; (b) Fürstner , A. ; Martin , R. Advances in iron catalyzed cross-coupling reactions . Chem. Lett. 2005 , 34 , 624 ; (c) Correa , A. ; Mancheñ , O. J. ; Bolm , C. Iron-catalysed carbon–heteroatom and heteroatom–heteroatom bond-forming processes . Chem. Soc. Rev. 2008 , 37 , 1108 – 1117 ; (d) Enthaler , S. ; Junge , K. ; Beller , M. Sustainable metal catalysis with iron: From rustto a rising star . Angew. Chem., Int. Ed. 2008 , 47 , 3317 – 3321 .
   PubMed Web of Science ®Google Scholar
• For a recent reviews, see (a) Miyaura , N. ; Suzuki , A. Palladium-catalyzed cross-coupling reactions of organoboron compounds . Chem. Rev. 1995 , 95 , 2457 – 2483 ; (b) Hassan , J. ; Sevignon , M. ; Gozzi , C. ; Schulz , E. ; Lemaire , M. Aryl-aryl bond formation one century after the discovery of the Ullmann reaction . Chem. Rev. 2002 , 102 , 1359 – 1470 ; (c) Chemler , S. R. ; Trauner , D. ; Danishefsky , S. J. The B-alkyl Suzuki–Miyaura cross-coupling reaction: Development, mechanistic study, and applications in natural product synthesis . Angew. Chem., Int. Ed. 2001 , 40 , 4544 – 4568 ; (d) Littke , A. F. ; Fu , G. C. Palladium-catalyzed coupling reactions of aryl chlorides . Angew. Chem., Int. Ed. 2002 , 41 , 4176 – 4211 ; (e) Nicolaou , K. C. ; Bulger , P. G. ; Sarlah , D. Palladium-catalyzed cross-coupling reactions in total synthesis . Angew. Chem., Int. Ed. 2005 , 44 , 4442 – 4489 ; (f) Phan , N. T. S. ; Sluys , M. V. D. ; Jones , C. W. On the nature of the active species in palladium-catalyzed Mizoroki–Heck and Suzuki–Miyaura couplings–homogeneous or heterogeneous catalysis, a critical review . Adv. Synth. Catal. 2006 , 348 , 609 – 679 ; (g) Nara , S. ; Martinez , J. ; Wermuth , C. G. ; Parrot , I. Palladium-catalysed cross-coupling reactions on pyridazine moieties . Synlett 2006 , 3185 – 3204 .
   Web of Science ®Google Scholar
• Tsuji , J. Palladium Reagents and Catalysts ; John Wiley & Sons : Chichester , UK , 2004 ; pp. 288 – 313 .
   Google Scholar
• For a recent review, see Knochel , P. ; Perea , J. J. A. ; Jones , P. Organozinc mediated reactions . Tetrahedron 1998 , 54 , 8275 – 8319 .
   Web of Science ®Google Scholar
• (a) Elliot , M. C. ; Williams , E. Saturated oxygen heterocycles . J. Chem. Soc., Perkin Trans. 2001 , 1 , 2303 – 2340 ; (b) Mitchinson , A. ; Nadin , A. Saturated nitrogen heterocycles . J. Chem. Soc., Perkin Trans. 2000 , 1 , 2862 – 2892 .
   Google Scholar
• (a) Zhang , Z. ; Widehoefer , R. A. Gold(I)-catalyzed intramolecular enantioselective hydroal-koxylation of allenes . Angew. Chem., Int. Ed. 2007 , 46 , 283 – 285 ; (b) Ma , S. Some typical advances in the synthetic applications of allenes . Chem. Rev. 2005 , 105 , 2829 – 2871 .
   PubMed Web of Science ®Google Scholar
• (a) Yao , T. ; Yue , D. ; Rarock , R. C. An efficient synthesis of coumestrol and coumestans by iodocyclization and Pd-catalyzed intramolecular lactonization . J. Org. Chem. 2005 , 70 , 9985 – 9989 ; (b) Yao , T. ; Yue , D. ; Rarock , R. C. Synthesis of 2,3-disubstituted benzo[b]furans by the palladium-catalyzed coupling of o-iodoanisoles and terminal alkynes, followed by electrophilic cyclization . J. Org. Chem. 2005 , 70 , 10292 – 10296 ; (c) Arimitsu , S. ; Jacobsen , J. M. ; Hammond , G. B. Synthesis of 2,4,5-trisubstituted 3-fluorofurans via sequential iodocyclization and cross-coupling of gem-difluorohomopropargyl alcohols . J. Org. Chem. 2008 , 73 , 2886 – 2889 .
   Google Scholar
• Heasley , V. L. ; Shellhamer , D. F. ; Heasley , L. E. ; Yaeger , D. B. Reactions of terminal alkynes with iodine in methanol . J. Org. Chem. 1980 , 45 , 4649 – 4652 .
   Google Scholar