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Synthesis 2011(10): 1581-1586
DOI: 10.1055/s-0030-1260009
DOI: 10.1055/s-0030-1260009
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkSynthesis of Biaryl Derivatives by Using Ruthenium-Mediated [2+2+2] Cyclotrimerization and Suzuki-Miyaura Cross-Coupling as Key Steps
Further Information
Received
10 February 2011
Publication Date:
19 April 2011 (online)
Publication History
Publication Date:
19 April 2011 (online)

Abstract
Functionalized biaryl derivatives have been prepared by applying [2+2+2] cyclotrimerization with the aid of Grubbs’ first-generation catalyst (G-I). The trimerized products were subjected to the Suzuki-Miyaura cross-coupling reaction sequence to generate highly functionalized biaryl derivatives.
Key words
terphenyl - quinquephenyl - [2+2+2] cyclotrimerization - Suzuki-Miyaura cross-coupling - metathesis
- 1a
Nicolaou KC.Boddy CNC.Brase S.Winssinger N. Angew. Chem. Int. Ed. 1999, 38: 2096MissingFormLabel - 1b
Hubbard BK.Walsh CT. Angew. Chem. Int. Ed. 2003, 42: 730MissingFormLabel - 1c
Kuroda M.Mimaki Y.Sakagami H.Sashida Y. J. Nat. Prod. 2003, 66: 894MissingFormLabel - 1d
Mutanyatta J.Bezabih M.Abegaz BM.Dreyer M.Brun R.Kocher N.Bringmann G. Tetrahedron 2005, 61: 8475MissingFormLabel - 1e
Cepanec I. Synthesis of Biaryls Elsevier; New York: 2004.MissingFormLabel - 2a
Brunel JM. Chem. Rev. 2005, 105: 857MissingFormLabel - 2b
Berthod M.Mignani G.Woodward G.Lemaire M. Chem. Rev. 2005, 105: 1801MissingFormLabel - 3
Pu L. Chem. Rev. 1998, 98: 2405 - 4a
Wallow TI.Novak BM. J. Am. Chem. Soc. 1991, 113: 7411MissingFormLabel - 4b
Elsenbaumer RL.Shacklette LW. Handbook of Conducting Polymers Vol. 1: Marcel Dekker; New York: 1986.MissingFormLabel - 5
Roncali J. Chem. Rev. 1992, 92: 711 - 6
Mei X.Wolf C. J. Am. Chem. Soc. 2006, 128: 13326 - 7a
Miyaura N.Suzuki A. Chem. Rev. 1995, 95: 2457MissingFormLabel - 7b
Stille JK.Lau KSY. Acc. Chem. Res. 1977, 10: 434MissingFormLabel - 7c
Negishi E.Anastasia L. Chem. Rev. 2003, 103: 1979MissingFormLabel - 7d
Kharasch MS.Fields EK. J. Am. Chem. Soc. 1941, 63: 2308MissingFormLabel - 7e
Kantam ML.Srinivas P.Yadav J.Likhar PR.Bhargava S. J. Org. Chem. 2009, 74: 4882MissingFormLabel - 7f
Srinivas P.Likhar PR.Maheswaran H.Sridhar B.Ravikumar K.Kantam ML. Chem. Eur. J. 2009, 15: 1578MissingFormLabel - 8a
Ashburn BO.Carter RG. Org. Biomol. Chem. 2008, 6: 255MissingFormLabel - 8b
Ashburn BO.Carter RG. Angew. Chem. Int. Ed. 2006, 45: 6737MissingFormLabel - 8c
Yamato T.Miyamoto M.Hironaka T.Miura Y. Org. Lett. 2005, 7: 3MissingFormLabel - 8d
Moore JE.York M.Harrity JPA. Synlett 2005, 860MissingFormLabel - 8e
Ram RN.Kumar N. Tetrahedron 2008, 64: 10267MissingFormLabel - 8f
Pearson AJ.Kim JB. Tetrahedron Lett. 2003, 44: 8525MissingFormLabel - 9a
Ramana CV.Suryawanshi SB. Tetrahedron Lett. 2008, 49: 445MissingFormLabel - 9b
Das SK.Roy R. Tetrahedron Lett. 1999, 40: 4015MissingFormLabel - 9c
Kotha S.Bansal D.Kumar RV. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2009, 48: 225MissingFormLabel - 9d
Yamamoto Y. Curr. Org. Chem. 2005, 9: 503MissingFormLabel - 9e
Ferrier RJ.Hoberg JO. Adv. Carbohydr. Chem. Biochem. 2003, 58: 55MissingFormLabel - 9f
Louiea J.Chopadea PR. Adv. Synth. Catal. 2006, 348: 2307MissingFormLabel - 9g
Tanaka K. Synlett 2007, 1977MissingFormLabel - 9h
Tanaka K. Chem. Asian J. 2009, 4: 508MissingFormLabel - 9i
Agenet N.Buisine O.Solwinski F.Gandon V.Aubert C.Malacria M. Org. React. 2007, 68:MissingFormLabel - 10
Takada T.Arisawa M.Gyoten M.Hamada R.Tohma H.Kita Y. J. Org. Chem. 1998, 63: 7698 - 11
Wetzel A.Ehrhardt V.Heinrich MR. Angew. Chem. Int. Ed. 2008, 47: 9130 - 12a
Hu B.Meng L.Liu Y.Liang M.Xue S. Synthesis 2009, 4137MissingFormLabel - 12b
Ullah I.Sher M.Khera RA.Ali A.Nawaz M.Shkoor M.Iqbal I.Imran M.Villinger A.Fischer C. Tetrahedron 2010, 66: 3824MissingFormLabel - 13a
Knappke CEI.Wangelin AJ. Angew. Chem. Int. Ed. 2010, 49: 2MissingFormLabel - 13b
Miguez JMA.Adrio LA.Pedrares AS.Vila JM.Hii KK. J. Org. Chem. 2007, 72: 7771MissingFormLabel - 14
Uchida I.Shigematsu N.Ezaki M.Hashimoto M.Aoki H.Imanaka H. J. Antibiot. 1985, 38: 1462 - 15
Schimana J.Gebhardt K.Holtzel A.Schmid DG.Sussmuth R.Muller RJ.Pukall R.Fiedler HP.
J. Antibiot. 2002, 55: 565 - 16a
Bird CW. Transition Metal Intermediates in Organic Synthesis Logos Press; London: 1967.MissingFormLabel - 16b
Vollhardt KPC. Acc. Chem. Res. 1977, 10: 1MissingFormLabel - 16c
Saito S.Yamamoto Y. Chem. Rev. 2000, 100: 2901MissingFormLabel - 16d
Gevorgyan V.Radhakrishnan U.Takeda A.Rubina M.Rubin M.Yamamoto Y. J. Org. Chem. 2001, 66: 2835MissingFormLabel - 17a
Lautens M.Klute W.Tam W. Chem. Rev. 1996, 96: 49MissingFormLabel - 17b
Volhardt KPC. Angew. Chem., Int. Ed. Engl. 1984, 23: 539MissingFormLabel - 17c
Maitles PM. Acc. Chem. Res. 1976, 9: 93MissingFormLabel - 17d
Trost BM.Tanoury GJ. J. Am. Chem. Soc. 1987, 109: 4753MissingFormLabel - 17e
Sneeden RPA.Zeiss HH. J. Organomet. Chem. 1971, 28: 259MissingFormLabel - 17f
Sato Y.Nishimata T.Mori M. J. Org. Chem. 1994, 59: 6133MissingFormLabel - 17g
Grigg R.Scott R.Stevenson P. Tetrahedron Lett. 1982, 23: 2691MissingFormLabel - 17h
Strickler JR.Bruck MA.Wigley DE. J. Am. Chem. Soc. 1990, 112: 2814MissingFormLabel - 17i
Slowinski F.Aubert C.Malacria M. Adv. Synth. Catal. 2001, 343: 64MissingFormLabel - 18a
Takao K.Tadano K. Heterocyclics 2010, 81: 1603MissingFormLabel - 18b
Lozano-Vila AM.Monsaert S.Bajek A. Chem. Rev. 2010, 110: 4865MissingFormLabel - 18c
Vougioukalakis GC.Grubbs RH. Chem. Rev. 2010, 110: 1746MissingFormLabel - 18d
Ben-Othman R.Othman M.Ciamala K. Tetrahedron 2009, 65: 4846MissingFormLabel - 18e
Buchmeiser MR. Chem. Rev. 2009, 109: 303MissingFormLabel - 18f
Burtscher D.Grela K. Angew. Chem. Int. Ed. 2009, 48: 442MissingFormLabel - 18g
Kurteva VB.Cam A. Chem. Rev. 2009, 109: 6809MissingFormLabel - 18h
Coquerel Y.Rodriguez J. Eur. J. Org. Chem. 2008, 1125MissingFormLabel - 19a
Grubbs RH.Schrock RR.Fürstner A. Adv. Synth. Catal. 2007, 349: 1MissingFormLabel - 19b
Dez-Gonzlez S.Marion M.Nolan SP. Chem. Soc. Rev. 2009, 109: 3612MissingFormLabel - 19c
Chauvin Y. Angew. Chem. Int. Ed. 2006, 45: 3741MissingFormLabel - 19d
Schrock RR. Angew. Chem. Int. Ed. 2006, 45: 3748MissingFormLabel - 19e
Grubbs RH. Angew. Chem. Int. Ed. 2006, 45: 3760MissingFormLabel - 19f
Nicolaou KC.Bulger PG.Sarlah D. Angew. Chem. Int. Ed. 2005, 44: 4490MissingFormLabel - 19g
Grubbs RH. Handbook of Metathesis Vols. 1-3: Wiley-VCH; Weinheim: 2003.MissingFormLabel - 20a
Kotha S.Seema V.Singh K.Deodher KD. Tetrahedron Lett. 2010, 51: 2341MissingFormLabel - 20b
Kotha S.Dipak MK. Chem. Eur. J. 2006, 12: 4446MissingFormLabel - 20c
Mori M. Adv. Synth. Catal. 2007, 349: 121MissingFormLabel - 20d
Maifeld SV.Lee D. Chem. Eur. J. 2005, 11: 6118MissingFormLabel - 20e
Subrahmanyam AV.Palanichamy K.Kaliappan KP. Chem. Eur. J. 2010, 16: 8545MissingFormLabel - 21a
Kotha S.Meshram M.Tiwari A. Chem. Soc. Rev. 2009, 38: 2065MissingFormLabel - 21b
Kotha S.Mandal K. Chem. Asian J. 2009, 4: 354MissingFormLabel - 21c
Kotha S.Khedkhar P. Synthesis 2008, 2925MissingFormLabel - 21d
Kotha S.Deb A. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2008, 47: 1120MissingFormLabel - 21e
Kotha S.Mandal K.Banerjee S. Eur. J. Org. Chem. 2007, 1244MissingFormLabel - 21f
Kotha S.Mandal K. J. Organomet. Chem. 2007, 629: 4921MissingFormLabel - 21g
Kotha S.Singh K. Eur. J. Org. Chem. 2007, 5909MissingFormLabel - 21h
Kotha S.Shah VR.Mandal K. Adv. Synth. Catal. 2007, 349: 1159MissingFormLabel - 21i
Kotha S.Mandal K.Tiwari A. Chem. Eur. J. 2006, 12: 8024MissingFormLabel - 21j
Kotha S.Sreenivasachary N. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2001, 40: 763MissingFormLabel - 22
Kotha S.Lahiri K.Kashinath D. Tetrahedron 2002, 58: 9632 - 23a
Kotha S.Khedkar P. Eur. J. Org. Chem. 2009, 730MissingFormLabel - 23b
Kotha S.Brahmachary E.Lahiri K. Eur. J. Org. Chem. 2005, 4741MissingFormLabel - 23c
Kotha S.Mohanraja K.Durani S. Chem. Commun. 2000, 1909MissingFormLabel - 23d
Kotha S.Brahmachary E. Tetrahedron Lett. 1997, 38: 3561MissingFormLabel - 24
Kotha S.Lahiri K. Synlett 2007, 18: 2767 - 25
Kotha S.Tafesh A.Davenport K.Ortiz P. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2001, 40: 1166 - 27
Liu L.Young B.Katz TJ.Poindexleron K. J. Org. Chem. 1991, 56: 3769
References
CCDC-797048 (7b) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.