Triflic Salt–Catalyzed Coupling: Iron Triflate–Catalyzed Homocoupling of Aryl Bromides in the Presence of Metallic Magnesium

REFERENCES

• Miyaura , N. Cross-Coupling Reactions. A Practical Guide Topics in Current Chemistry ; Springer : Berlin , 2002 .
   Google Scholar
• Li , J. J. ; Gribble , G. W. Palladium in Heterocyclic Chemistry: A Guide for the Synthetic Chemist ; Elsevier : Oxford , 2000 .
   Google Scholar
• Suzuki , A. Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles . J. Organomet. Chem. 1999 , 576 ( 1–2 ), 147 – 168 .
   Web of Science ®Google Scholar
• Duncton , M. A. J. ; Pattenden , G. The intramolecular Stille reaction . J. Chem. Soc., Perkin Trans. 1 1999 , 10 , 1235 – 1246 .
   Google Scholar
• Diederich , F. ; Stang , P. J. Metal-Catalyzed Cross-Coupling Reactions ; Wiley-VCH : Weinheim , Germany , 1998 .
   Google Scholar
• Knight , D. W. In Comprehensive Organic Synthesis ; B. M. Trost , I. Fleming (Eds.); Pergamon : Oxford , 1991 ; vol. 3 , p. 481 .
   Google Scholar
• Stille , J. K. The palladium-catalyzed cross-coupling reactions of organotin reagents with organic electrophiles . Angew. Chem., Int. Ed. Engl. 1986 , 25 ( 6 ), 508 – 524 .
   Web of Science ®Google Scholar
• Sainsbury , M. Modern methods of aryl–aryl bond formation . Tetrahedron 1980 , 36 ( 23 ), 3327 – 3359 .
   Web of Science ®Google Scholar
• Fanta , P. E. The Ullmann synthesis of biaryls . Chem. Rev. 1946 , 38 ( 1 ), 139 – 196 .
   PubMed Web of Science ®Google Scholar
• Fanta , P. E. The Ullmann synthesis of biaryls, 1945–1963: The asymmetric Ullmann reaction, 2: The synthesis of enantiomerically pure C2-symmetric binaphthyls . Chem. Rev. 1964 , 64 ( 6 ), 613 – 632 .
   Web of Science ®Google Scholar
• Posner , G. H. An Introduction to Synthesis Using Organocopper Reagents ; John Wiley : New York , 1980 .
   Google Scholar
• Nelson , T. D. ; Meyers , A. I. The asymmetric Ullmann reaction, 2: The synthesis of enantiomerically pure C2-symmetric binaphthyls . J. Org. Chem. 1994 , 59 ( 9 ), 2655 – 2658 .
   Web of Science ®Google Scholar
• Nicolaou , K. C. ; Hanko , R. ; Hartwig , W. (Eds). Handbook of Combinatorial Chemistry: Drugs, Catalysts, Materials ; Wiley-VCH : Weinheim , Germany , 2002 .
   Google Scholar
• Negishi , E. (Ed.). Handbook of Organopalladium Chemistry for Organic Synthesis ; Wiley : New York , 2002 .
   Google Scholar
• Tsuji , J. Palladium Reagents and Catalysts: Innovations in Organic Synthesis ; Wiley : New York , 1996 .
   Google Scholar
• Kochi , J. K. Homo coupling, disproportionation, and cross coupling of alkyl groups: Role of the transition metal catalyst . J. Organomet. Chem. 2002 , 653 ( 1–2 ), 11 – 19 .
   Google Scholar
• Smith , R. S. ; Kochi , J. K. Mechanistic studies of iron catalysis in the cross coupling of alkenyl halides and Grignard reagents. J. Org. Chem. 1976, 41(3), 502–509.
   Web of Science ®Google Scholar
• Neumann , S. M. ; Kochi , J. K. Synthesis of olefins: Cross-coupling of alkenyl halides and Grignard reagents catalyzed by iron complexes . J. Org. Chem. 1975 , 40 ( 5 ), 599 – 606 .
   Web of Science ®Google Scholar
• Tamura , M. ; Kochi , J. K. Vinylation of Grignard reagents: Catalysis by iron . J. Am. Chem. Soc. 1971 , 93 ( 6 ), 1487 – 1489 .
   Web of Science ®Google Scholar
• Tamura , M. ; Kochi , J. K. The reactions of Grignard reagents with transition metal halides: Coupling, disproportionation, and exchange with olefins . Bull. Chem. Soc. Jpn. 1971 , 44 ( 11 ), 3063 – 3073 .
   Web of Science ®Google Scholar
• Tamura , M. ; Kochi , J. K. Coupling of Grignard reagents with organic halides . Synthesis 1971 , 6 , 303 – 304 .
   Google Scholar
• Fuerstner , A. ; Martin , R. Advances in iron-catalyzed cross-coupling reactions . Chem. Lett. 2005 , 34 ( 5 ), 624 – 629 .
   Web of Science ®Google Scholar
• Shinokubo , H. ; Oshima , K. E. Transition metal–catalyzed carbon–carbon bond formation with Grignard reagents: Novel reactions with a classic reagent . J. Org. Chem. 2004 , 2004 ( 10 ), 2081 – 2091 .
   Google Scholar
• Bolm , C. ; Legros , J. ; Le , P. J. ; Zani , L. Iron-catalyzed reactions in organic synthesis . Chem. Rev. 2004 , 104 ( 12 ), 6217 – 6254 .
   PubMed Web of Science ®Google Scholar
• Bica , K. ; Gaertner , P. An iron-containing ionic liquid as recyclable catalyst for aryl Grignard cross-coupling of alkyl halides . Org. Lett. 2006 , 8 ( 4 ), 733 – 735 .
   PubMed Web of Science ®Google Scholar
• Bedford , B. R. ; Betham , M. ; Bruce , W. D. ; Danopoulos , A. A. ; Frost , M. R. ; Hird , M. Iron-phosphine, -phosphite, -arsine, and -carbene catalysts for the coupling of primary and secondary alkyl halides with aryl Grignard reagents . J. Org. Chem. 2006 , 71 ( 3 ), 1104 – 1110 .
   PubMed Web of Science ®Google Scholar
• Bedford , B. R. ; Bruce , W. D. ; Frost , M. R. Simple iron-amine catalysts for the cross-coupling of aryl Grignards with alkyl halides bearing β-hydrogens . Chem. Commun. 2005 , 33 , 4161 – 4163 .
   Google Scholar
• Bedford , B. R. ; Bruce , W. D. ; Frost , M. R. Iron(III) salen-type catalysts for the cross-coupling of aryl Grignards with alkyl halides bearing β-hydrogens . Chem. Commun. 2004 , 24 , 2822 – 2823 .
   Google Scholar
• Martin , R. ; Fürstner , A. Cross-coupling of alkyl halides with aryl Grignard reagents catalyzed by a low-valent iron complex . Angew. Chem., Int. Ed. 2004 , 43 ( 30 ), 3955 – 3957 .
   PubMed Web of Science ®Google Scholar
• Nagano , T. ; Hayashi , T. Iron-catalyzed Grignard cross-coupling with alkyl halides possessing β-hydrogens . Org. Lett. 2004 , 6 ( 8 ), 1297 – 1299 .
   PubMed Web of Science ®Google Scholar
• Hojo , M. ; Murakami , Y. ; Aihara , H. Iron-catalyzed regio- and stereoselective carbolithiation of alkynes . Angew. Chem., Int. Ed. 2001 , 40 ( 3 ), 621 – 623 .
   Web of Science ®Google Scholar
• Nakamura , M. ; Hirai , A. ; Nakamura , E. Iron-catalyzed olefin carbometalation . J. Am. Chem. Soc. 2000 , 122 ( 5 ), 978 – 979 .
   Web of Science ®Google Scholar
• Cahiez , G. ; Avedissian , H. Synthesis of functionalized triphenylenes by selective ether cleavage with β-bromocatecholborane . Synthesis 1998 , 8 , 1199 – 1122 .
   Google Scholar
• Yanagisawa , A. ; Nomura , N. ; Yamamoto , H. Transition metal–catalyzed substitution reaction of allylic phosphates with Grignard reagents . Tetrahedron 1994 , 50 ( 20 ), 6017 – 6028 .
   Web of Science ®Google Scholar
• Yanagisawa , A. ; Nomura , N. ; Yamamoto , H. Iron-catalyzed Kharasch-type reaction between Grignard reagents and allylic phosphates: Highly SN2 selective cross-coupling process . Synlett 1991 , 7 , 513 – 515 .
   Google Scholar
• Nagano , T. ; Hayashi , T. Iron-catalyzed oxidative homo-coupling of aryl Grignard reagents . Org. Lett. 2005 , 7 ( 3 ), 491 – 493 .
   PubMed Web of Science ®Google Scholar
• Cahiez , G. ; Chaboche , C. ; Mahuteau-Betzer , F. ; Ahr , M. Iron-catalyzed homo-coupling of simple and functionalized arylmagnesium reagents . Org. Lett. 2005 , 7 ( 10 ), 1943 – 1946 .
   PubMed Web of Science ®Google Scholar
• Xu , X. ; Cheng , D. ; Pei , W. Iron-catalyzed homocoupling of bromide compounds . J. Org. Chem. 2006 , 71 ( 17 ), 6637 – 6639 .
   PubMed Web of Science ®Google Scholar
• Kobayashi , S. ; Sugiura , M. ; Kitagawa , H. ; William , W. L. Rare-earth metal triflates in organic synthesis. Chem. Rev. 2002, 102(6), 2227–2302.
   PubMed Web of Science ®Google Scholar
• Zhang , C. ; Cheng , T. ; Li , R. M(OTf)3-catalyzed novel Mannich reaction of N-alkyoxycarbonylpyrrole or thiophene, formaldehyde, and primary amine hydrochloride . Acta Chim. Sinica 2002 , 60 ( 3 ), 481 – 486 .
   Web of Science ®Google Scholar
• Li , X. ; Du , X. ; Xu , Z. Toluene nitration catalyzed by metal triflates . Chin. J. Org. Chem. 2006 , 26 ( 8 ), 1111 – 1114 .
   Web of Science ®Google Scholar
• Lin , J. ; Zheng , Y. ; Li , J. Preparation of (E)-6-(3-methyl-4-benzenesulfonyl-2-butenyl)-2,3,4,5-tetramethoxytoluene in the presence of trifluoromethanesulfonic salt . J. Zhejiang Univ. Technol. 2007 , 35 ( 2 ), 190 – 193 .
   Google Scholar
• Ma , N. ; Zhu , Z. ; Wu , Y. Cyclopalladated ferrocenylimine: A highly effective catalyst for the borylation Suzuki coupling reaction . Tetrahedron 2007 , 63 ( 22 ), 4625 – 4629 .
   Web of Science ®Google Scholar
• Wang , L. ; Zhang , Y. ; Liu , L. Palladium-catalyzed homocoupling and cross-coupling reactions of aryl halides in poly(ethylene glycol) . J. Org. Chem. 2006 , 71 ( 3 ), 1284 – 1287 .
   PubMed Web of Science ®Google Scholar
• Tashiro , M. ; Yamato , T. Studies on selective preparation of aromatic compounds, 20: Selective preparation of 2-mono- and 2,2′-disubstituted biphenyl using the tert-butyl group as a positional protective group . J. Org. Chem. 1979 , 44 ( 17 ), 3037 – 3040 .
   Web of Science ®Google Scholar
• Taylor , S. K. ; Bennett , S. G. ; Heinz , K. J. Coupling of aryl Grignard reagents by electron transfer to unsaturated 1,4-dihalo compounds . J. Org. Chem. 1981 , 46 ( 10 ), 2194 – 2196 .
   Web of Science ®Google Scholar