Synthesis of bis(diaryl)sulfones by site-selective suzuki-miyaura reactions of 2,4-bis(trifluoromethylsulfonyloxy)diphenylsulfone

Synlett

Volumn , Issue 5, 2010, Pages 731-734

  Ali, Asad ^a   Khera, Rasheed Ahmad ^a   Ibad, Muhammad Farooq ^a   Hussain, Munawar ^a   Langer, Peter ^a,b  

^a UNIVERSITY OF ROSTOCK   (Germany)

^b LEIBNIZ INSTITUT FÜR KATALYSE E V AN DER UNIVERSITÄT ROSTOCK   (Germany)

Author keywords

Catalysis; Palladium; Site selectivity; Sulfones; Suzuki Miyaura reaction

Indexed keywords

2,4' BIS(TRIFLUOROMETHYLSULFONYLOXY)DIPHENYLSULFONE; BIS(DIARYL)SULFONE DERIVATIVE; BORONIC ACID DERIVATIVE; SULFONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; SUZUKI REACTION;

EID: 77749293042     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1219343     Document Type: Article

References (10)

1. 1 receptor:, Lavey B J., Kozlowski J A., Hipkin R W., Gonsiorek W, Lundell D J., Piwinski J J., Narula S, Lunn C A., Bioorg. Med. Chem. Lett. 2005 15 783 Inhibition of the main protease of the recombinant SARS coronavirus:, Lu I.-L, Mahindroo N, Liang P.-H, Peng Y.-H, Kuo C.-J, Tsai K.-C, Hsieh H.-P, Chao Y.-S, Wu S.-Y, J. Med. Chem. 2006 9 5154
2. Joseph J K., Jain S L., Sain B, Synth. Commun. 2006 36 2743
3. Chen D.-W, Kubiak R J., Ashley J A., Janda K D., J. Chem. Soc., Perkin Trans. 1 2001 21 2796, Marquie J, Laporterie A, Dubac J, Roques N, Desmurs J.-R, J. Org. Chem. 2001 66 421, Repichet S, LeRoux C, Dubac J, Tetrahedron Lett. 1999 40 9233, Hajipour A R., Zarei A, Khazdooz L, Pourmousavi S A., Mirjalili B B. F., Ruoho A E., Phosphorus, Sulfur Silicon Relat. Elem. 2005 180 2029
4. Woroshzow V, Kutschkarow V, Zh. Obshch. Khim. 1949 19 1943; Chem. Abstr. 1950, 1922
5. Zhu W, Ma D, J. Org. Chem. 2005 70 2696
6. Bandgar B P., Bettigeri S V., Phopase J, Org. Lett. 2004 6 2105
7. Huang F, Batey R A., Tetrahedron 2007 63 7667
8. Erian A W., Issac Y, Sherif S M., Mahmoud F F., J. Chem. Soc., Perkin Trans. 1 2000 3686, Ogura K, Takeda M, Xie J R., Akazome M, Matsumoto S, Tetrahedron Lett. 2001 42 1923, Matsumoto S, Kumazawa K, Ogura K, Bull. Chem. Soc. Jpn. 2003 76 2179, Bianchi L, DellErba C, Maccagno M, Mugnoli A, Novi M, Petrillo G, Sancassan F, Tavani C, J. Org. Chem. 2003 68 5254, Mutsuhiro Y, Watanabe M, Furukawa S, Chem. Pharm. Bull. 1990 38 902, Padwa A, Gareau Y, Harrison B, Rodriguez A, J. Org. Chem. 1992 57 3540, Hayakawa K, Nishiyama H, Kanematsu K, J. Org. Chem. 1985 50 512, Nakayama J, Hirashima A, J. Am. Chem. Soc. 1990 112 7648, Hu C.-M, Hong F, Jiang B, Xu Y, J. Fluorine Chem. 1994 66 215, Antelo B, Castedo L, Delamano J, Gomes A, Lopez C, Tojo G, J. Org. Chem. 1996 61 1188, Shkoor M, Riahi A, Fatunsin O, Reinke H, Fischer C, Langer P, Synthesis 2009 2223
9. For a review of site-selective palladium(0)-catalyzed cross-coupling reactions, see:, Schröter S, Stock C, Bach T, Tetrahedron 2005 61 2245
10. For site-selective reactions of bis(triflates) of 2,4-dihydro- xybenzophenones, see:, Nawaz M, Adeel M, Farooq M, Langer P, Synlett 2009 2154 For reactions of the bis(triflate) of methyl 2,5-dihydroxybenzoate, see:, Nawaz M, Farooq M, Obaid-Ur-Rahman A, Khera R A., Villinger A, Langer P, Synlett 2010 150