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Synthesis 2010(12): 2005-2010
DOI: 10.1055/s-0029-1218759
DOI: 10.1055/s-0029-1218759
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkCopper(II)-Catalyzed Esterification of Arenecarboxylic Acids with Aryl- and Vinyl-Substituted Trimethoxysilanes
Weitere Informationen
Received
24 February 2010
Publikationsdatum:
29. April 2010 (online)
Publikationsverlauf
Publikationsdatum:
29. April 2010 (online)
Abstract
In this paper, the copper(II)-catalyzed esterification reaction of arenecarboxylic acids with aryl- or vinyl-substituted trimethoxysilanes is described. A series of aryltrimethoxysilanes and arenecarboxylic acids worked well under this procedure, affording aryl benzoate derivatives in moderate to good yields. Notably, trimethoxy(vinyl)silanes also worked well under this procedure giving a facile and versatile method to access vinyl benzoate derivatives.
Key words
copper(II) catalyzed - trimethoxysilanes - carboxylic acids - esters - silver(I) fluoride
- Supporting Information for this article is available online:
- Supporting Information
- 1a
Moretto A.Nicolli A.Lotti M. Toxicol. Appl. Pharm. 2007, 219: 196 - 1b
Beginn U.Zipp G.Moller M. Chem. Eur. J. 2000, 6: 2016 - 1c
Barratt MD.Basketter DA.Roberts DW. Toxicol. Vitro 1994, 8: 823 - 1d
Child JJ.Oka T.Simpson FJ.Krishnamurty HG. Can. J. Microbiol. 1971, 17: 1455 - 1e
Berndt MC.Bowles MR.King GJ.Zerner B. Biochim. Biophys. Acta 1996, 1298: 159 - 2a
Ishihara K. Tetrahedron 2009, 65: 1085 - 2b
Konwar D.Gogoi PK.Gogoi P.Borah G.Baruah R.Hazarika N.Borgohain R. Indian J. Chem. Technol. 2008, 15: 75 - 2c
Vijayakumar B.Iyengar P.Nagendrappa G.Prakash BSJ. J. Indian Chem. Soc. 2005, 82: 922 - 2d
Lee CK.Yu JS.Lee H.-J. J. Heterocycl. Chem. 2002, 39: 1207 - 2e
Eshghi H.Rafei M.Karimi MH. Synth. Commun. 2001, 31: 771 - 2f
Ueda M.Mori H. Bull. Chem. Soc. Jpn. 1992, 65: 1636 - 2g
Ueda M.Oikawa H. J. Org. Chem. 1985, 50: 760 - 2h
Keshavamurthy KS.Vankar YD.Dhar DN. Synthesis 1982, 506 - 2i
Lawrence WW. Tetrahedron Lett. 1971, 12: 3453 - 3a
Khalfina IA.Vlasov VM. Russ. J. Org. Chem. (Engl. Transl.) 2008, 44: 1619 - 3b
Oohashi Y.Fukumoto K.Mukaiyama T. Bull. Chem. Soc. Jpn. 2005, 78: 1508 - 3c
Degani I.Dughera S.Fochi R.Serra E. Synthesis 1999, 1200 - 4a
Fischer E. Ber. Dtsch. Chem. Ges. 1895, 28: 3254 - 4b
Butts J. J. Am. Chem. Soc. 1931, 53: 3560 - 5a
Olah GA.Wang Q.Trivedi NJ.Prakash GKS. Synthesis 1991, 739 - 5b
Yadav JS.Reddy BVS.Basak AK.Narsaiah AV. Chem. Lett. 2004, 33: 248 - 5c
Kotsuki H.Arimura K.Araki T.Shinohara T. Synlett 1999, 462 - 5d
Toda F.Yagi M.Kiyoshige K. J. Chem. Soc., Chem. Commun. 1988, 958 - 6a
Qin C.Wu H.Chen J.Liu M.Cheng J.Su W.Ding J. Org. Lett. 2008, 10: 1537 - 6b
Kiyooka S.-I.Wada Y.Ueno M.Yokoyama T.Yokoyama R. Tetrahedron 2007, 63: 12695 - 6c
Gopinath R.Patel BK. Org. Lett. 2000, 2: 577 - 6d
Barkakaty B.Talukdar B.Patel BK. J. Org. Chem. 2003, 68: 2944 - 6e
Travis BR.Sivakumar M.Hollist GO.Borhan B. Org. Lett. 2003, 5: 1031 - 6f
Gopinath R.Paital AR.Patel BK. Tetrahedron Lett. 2002, 43: 5123 - 6g
McDonald CE.Nice LE.Shaw AW.Nestor NB. Tetrahedron Lett. 1993, 34: 2741 - 6h
Han R.Hillhouse GL. J. Am. Chem. Soc. 1997, 119: 8135 - 6i
Espenson JH.Zhu Z.Zauche TH. J. Org. Chem. 1999, 64: 1191 - 7
Nakatani Y.Koizumi Y.Yamasaki R.Saito S. Org. Lett. 2008, 10: 2067 - For selected references, see:
- 8a
Lam PYS.Clark CG.Saubern S.Adams J.Winters MP.Chan DMT.Combs A. Tetrahedron Lett. 1998, 39: 2941 - 8b
Combs A.Saubern S.Rafalski M.Lam PYS. Tetrahedron Lett. 1999, 40: 1623 - 8c
Lam PYS.Clark CG.Saubern S.Adams J.Averill KM.Chan DMT.Combs A. Synlett 2000, 674 - 8d
Kantam ML.Venkanna GT.Sridhar C.Sreedhar B.Choudary BM. J. Org. Chem. 2006, 71: 9522 - 8e
Quach TD.Batey RA. Org. Lett. 2003, 5: 4397 - 8f
Sreedhar B.Venkanna GT.Kumar KBS.Balasubrahmanyam V. Synthesis 2008, 795 - 8g
Zhou C.Yang D.Jia X.Zhang L.Cheng J. Synlett 2009, 3198 - For selected references, see:
- 9a
Chan DMT.Monaco KL.Wang R.-P.Winters MP. Tetrahedron Lett. 1998, 39: 2933 - 9b
Evans DA.Katz JL.West TR. Tetrahedron Lett. 1998, 39: 2937 - 9c
Quach TD.Batey RA. Org. Lett. 2003, 5: 1381 - 9d
Lam PYS.Vincent G.Bonne D.Clark CG. Tetrahedron Lett. 2003, 44: 4927 - 9e
Chan DMT.Monaco KL.Li R.Bonne D.Clark CG.Lam PYS. Tetrahedron Lett. 2003, 44: 3863 - 9f
Lam PYS.Vincent G.Clark CG.Deudon S.Jadhav PK. Tetrahedron Lett. 2001, 42: 3415 - 10a
Li J.-H.Deng CL.Xie YX. Synthesis 2006, 969 - 10b
Shi SY.Zhang YH. J. Org. Chem. 2007, 72: 5927 - 10c
Pan C.Liu M.Zhao L.Wu H.Ding J.Cheng J. Catal. Commun. 2008, 9: 1685 - 10d
Dey R.Chattopadhyay K.Ranu BC. J. Org. Chem. 2008, 73: 9461 - 10e
So CM.Lee HW.Lau CP.Kwong FY. Org. Lett. 2009, 11: 317 - 10f
Zhang L.Qing J.Yang P.Wu J. Org. Lett. 2008, 10: 4971 - 10g
Zhang L.Wu J. J. Am. Chem. Soc. 2008, 130: 12250 - 10h
Lerebours R.Wolf C. Org. Lett. 2007, 9: 2737 - 10i
Ye Z.Liu M.Lin B.Wu H.Ding J.Cheng J. Tetrahedron Lett. 2009, 50: 530 - 10j
Lin B.Liu M.Ye Z.Zhang Q.Cheng J. Tetrahedron Lett. 2009, 50: 1714 - 10k
Ye Z.Chen F.Luo F.Wang W.Lin B.Jia X.Cheng J. Synlett 2009, 2198 - 10l
Yang S.Li B.Wan X.Shi Z. J. Am. Chem. Soc. 2007, 129: 6066 - 11a
Lin B.Liu M.Ye Z.Ding J.Wu H.Cheng J. Org. Biomol. Chem. 2009, 7: 869 - 11b
Pan C.Cheng J.Wu H.Ding J.Liu M. Synth. Commun. 2009, 39: 2082 - 11c
Song R.-J.Deng C.-L.Xie Y.-X.Li J.-H. Tetrahedron Lett. 2007, 48: 7845 - 11d
Lam PYS.Deudon S.Averill KM.Li R.He MY.DeShong P.Clark CG. J. Am. Chem. Soc. 2000, 122: 7600 - 11e
Lam PYS.Deudon S.Hauptman E.Clark CG. Tetrahedron Lett. 2001, 42: 2427 - 12
Luo P.-S.Yu M.Tang R.-Y.Zhong P.Li J.-H. Tetrahedron Lett. 2009, 50: 1066 - 13a
Petrassi HM.Sharpless KB.Kelly JW. Org. Lett. 2001, 3: 139 - 13b
Decicco CP.Song Y.Evans DA. Org. Lett. 2001, 3: 1029 - 13c
Jung ME.Lazarova TI. J. Org. Chem. 1999, 64: 2976 - 13d
Blouin M.Frenette R. J. Org. Chem. 2001, 66: 9043 - 13e
Finet JP. Chem. Rev. 1989, 89: 1487 - 14
Lerebours R.Wolf C. J. Am. Chem. Soc. 2006, 128: 13052 - 15
Hudrlik PF.Hudrlik AM. J. Org. Chem. 1973, 38: 4254 - 16a
Kawano H.Masaki Y.Matsunaga T.Hiraki K.Onishi M.Tsubomura T. J. Organomet. Chem. 2000, 604: 69 - 16b
Bruneau C.Dixneuf PH. Chem. Commun. 1997, 507 - 16c
Doucet H.Martin-Vaca B.Bruneau C.Dixneuf PH. J. Org. Chem. 1995, 60: 7247 - 16d
Rotem M.Shvo Y. Organometallics 1983, 2: 1689 - 17
Nakagawa H.Okimoto Y.Sakaguchi S.Ishii Y. Tetrahedron Lett. 2003, 44: 103 - 20
King AE.Brunold TC.Stahl SS. J. Am. Chem. Soc. 2009, 131: 5044 - 21
Won J.-E.Kim H.-K.Kim J.-J.Yim H.-S.Kim M.-J.Kang S.-B.Chung H.-A.Lee S.-G.Yoon Y.-J. Tetrahedron 2007, 63: 12720 - 22
Iranpoor N.Firouzabadi H.Khalili D.Motevalli S.
J. Org. Chem. 2008, 73: 4882 - 23
Ross J.Xiao J. Green Chem. 2002, 4: 129 - 24
Ishihara K.Nakayama M.Ohara S.Yamamoto H. Tetrahedron 2002, 58: 8179 - 25
Barbero M.Cadamuro S.Dughera S.Venturello P. Synthesis 2008, 3625 - 26
Song G.Cai Y.Peng Y. J. Comb. Chem. 2005, 7: 561 - 27
Roy HN.Al Mamun AH. Synth. Commun. 2006, 36: 2975 - 28
Liu Z.Larock RC. J. Org. Chem. 2006, 71: 3198 - 29
Neuvonen H.Neuvonen K.Pasanen P. J. Org. Chem. 2004, 69: 3794 - 30
Yoshida H.Mimura Y.Ohshita J.Kunai A. Chem. Commun. 2007, 2405 - 31
Ramesh C.Kubota Y.Miwa M.Sugi Y. Synthesis 2002, 2171 - 32
Williams FJ. J. Org. Chem. 1977, 42: 3425 - 33
van Paesschen G. Makromol. Chem. 1960, 37: 46 - 34
Chhor RB. Synth. Commun. 2003, 33: 2519 - 35
Ham GE. J. Polym. Sci. 1952, 8: 91 - 36
Lussi H. Kuntst.-Plast. 1956, 3: 156 - 37
Trost BM.Malhotra S.Mino T.Rajapaksa NS. Chem. Eur. J. 2008, 14: 7648 - 38
Shostakovskii MF.Komarova LI. Zh. Prikl. Khim. 1966, 39: 725 - 39
Levchenko AI.Nanasenko BF.Khorunzhii AP. Dokl. Vses. Konf. Khim. Atsetilena 1972, 4: 2414
References
For the transfer of phenyl from trimethoxy(phenyl)silane to copper(II), see refs 11c-e.
19The formation of a Ag(0) film was observed. We reasoned that Cu(0) is produced after reductive elimination and is then oxidized to Cu(II) by Ag(I).