Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2011(16): 2329-2334
DOI: 10.1055/s-0030-1260315
DOI: 10.1055/s-0030-1260315
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
Diversity-Oriented Synthesis of Biaryl Derivatives Using Cross-Enyne Metathesis, Diels-Alder Reaction, and Suzuki-Miyaura Cross-Coupling as Key Steps
Further Information
Received
26 May 2011
Publication Date:
13 September 2011 (online)
Publication History
Publication Date:
13 September 2011 (online)
Abstract
Biaryl derivatives have been prepared by utilizing cross-enyne metathesis, Diels-Alder reaction followed by aromatization. These biaryl derivatives are further functionalized via Suzuki-Miyaura cross-coupling reaction to generate functionalized terphenyl derivatives.
Key Words
biaryl derivatives - cross-enyne metathesis - Suzuki-Miyaura cross-coupling - diversity-oriented synthesis
-
1a
Herbert W.Yu-Peng H.Hao T.Lars AA.Hans-Dieter A. Chem. Commun. 2008, 5562 -
1b
Nussbaum FV.Brands M.Hinzen B.Weigand S.Habich D. Angew. Chem. Int Ed. 2006, 45: 5072 -
1c
Hassan J.Sevignon M.Gozzi C.Schulz E.Lemaire M. Chem. Rev. 2002, 102: 1359 -
1d
Bringmann M.Gunther C.Ochse M.Schupp O.Tasler S. J. Nat. Prod. 2001, 82: 249 - 2
Horton DA.Bourne GT.Smythe ML. Chem. Rev. 2003, 103: 893 - 3
Larsen RD.King A.Chen CY.Corley EG.Foster BS.Roberts FE.Yang C.Lieberman DR.Reamer RA.Tschaen DM.Verhoeven TR.Reider PJ. J. Org. Chem. 1994, 59: 6391 -
4a
Glascalid TN.Kappe CO. Adv. Synth. Catal. 2010, 352: 3089 -
4b
Goosen LJ.Thomas K. J. Org. Chem. 2008, 73: 8631 -
4c
Bhowmik S.Horsman GP.Bolin JT. J. Biol. Chem. 2007, 282: 36377 -
4d
Tsunoda T.Yamazaki A.Mase T.Sakamoto S. Org. Process Res. Dev. 2005, 9: 593 -
4e
Cepanec I. Synthesis of Biaryls Elsevier; New York: 2004. -
4f
Bringmann G.Menche D. Angew. Chem. Int. Ed. 2001, 40: 1687 -
4g
Kamikawa K.Watanabe T.Daimon A.Uemura M. Tetrahedron 2000, 56: 2325 -
5a
Bhalla V.Tejpal R.Kumar M.Seth A. Inorg. Chem. 2009, 48: 11677 -
5b
Bhalla V.Kumar M. Org. Lett. 2010, 12: 628 -
5c
Stille JK. Angew. Chem., Int. Ed. Engl. 1986, 25: 508 -
6a
Venuti MC. J. Org. Chem. 1981, 46: 3124 -
6b
Kolotuchin SV.Meyers AI. J. Org. Chem. 1999, 64: 7921 -
6c
McCarthy M.Guiry PJ. Tetrahedron 2001, 57: 3809 - 7
Noyori R.Takaya H. Acc. Chem. Res. 1990, 23: 345 -
8a
Handbook of Organopalladium Chemistry for
Organic Synthesis
Negishi E.de Meijere A. Wiley Interscience; New York: 2002. -
8b
Metal-Catalyzed
Cross-Coupling Reactions
Vol. 1 and 2:
de Meijere A.Diederich F. Wiley-VCH; Weinheim: 2004. -
8c
Kotha S.Brahmachary E.Lahiri K. Eur. J. Org. Chem. 2005, 4741 -
8d
Liu CY.Gavryushin A.Knochel P. Chem. Asian J. 2007, 2: 1020 - For recent reviews please, see:
-
9a
Kotha S.Lahiri K. Synlett 2007, 2767 -
9b
Grubbs RH. Tetrahedron 2004, 60: 7117 -
9c
Deiters A.Martin SF. Chem. Rev. 2004, 104: 2199 -
9d
McReynolds MD.Dougherty JM.Hanson PR. Chem. Rev. 2004, 104: 2239 -
9e
Schrock RR.Hoveyda AH. Angew. Chem. Int. Ed. 2003, 42: 4592 -
9f
Kotha S.Sreenivasachary N. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2001, 40: 763 -
9g
Samojowicz C.Bieniek M.Grela K. Chem. Rev. 2009, 109: 3708 -
10a
Kotha S.Seema V.Singh K.Deodher KD. Tetrahedron Lett. 2010, 51: 2341 -
10b
Kotha S.Shah VR.Mandal K. Adv. Synth. Catal. 2007, 1159 -
10c
Kotha S.Dipak MK. Chem. Eur. J. 2006, 12: 4446 -
10d
Kotha S.Mandal K. Tetrahedron Lett. 2004, 45: 2585 -
11a
Kotha S.Meshram M.Tiwari A. Chem. Soc. Rev. 2009, 38: 2065 -
11b
Kotha S.Mandal K. Chem. Asian. J. 2009, 4: 354 -
11c
Kotha S.Mandal K.Banerjee S.Mobin SM. Eur. J. Org Chem. 2007, 1244 -
12a
Fringulli F.Taticchi A. Dienes in the Diels-Alder Reaction Wiley; New York: 1990. -
12b
Paquette LA. Comprehensive Organic Synthesis Vol. 5: Pergamon; Oxford: 1991. -
12c
Kaliappan KP.Velayutham R. J. Org. Chem. 2007, 72: 6116 -
12d
Hansen EC.Lee D. Acc. Chem. Res. 2006, 39: 509 -
12e
Jayakanthan K.Vankar YD. Org. Lett. 2005, 7: 5441 -
12f
Diver ST.Giessert AJ. Chem. Rev. 2004, 104: 1317 -
12g
Poulsen CS.Madsen R. Synthesis 2003, 1 -
12h
Mori M. Top. Organomet. Chem. 1999, 1: 133 -
13a
Kotha S.Khedkhar P. Synthesis 2008, 2925 -
13b
Kotha S.Singh K. Eur. J. Org. Chem. 2007, 5909 -
13c
Middleton MD.Peppers B.Diver S. Tetrahedron 2006, 62: 10528 -
13d
Middleton MD.Diver S. Tetrahedron Lett. 2005, 46: 4039 -
13e
Tonogaki K.Mori M. Tetrahedron Lett. 2002, 43: 2235 -
13f
Smulik JA.Diver S. Org. Lett. 2000, 2: 2271 -
13g
Schwab P.France MB.Ziller JW.Grubbs RH. Angew. Chem., Int. Ed. Engl. 1995, 34: 2039 -
14a
Kotha S.Chavan S. J. Org. Chem. 2010, 75: 4319 -
14b
Kotha S.Khedkher P. J. Org. Chem. 2009, 74: 5667 -
14c
Ikeuchi Y.Saitoh T.Taguchi T.Hanzawa Y. Tetrahedron Lett. 2007, 48: 2477 -
15a
Kotha S.Lahiri K. Eur. J. Org. Chem. 2007, 1221 -
15b
Kotha S.Mandal K.Arora KK.Pedireddi VV. Adv. Synth. Catal. 2005, 347: 1215 -
15c
Kotha S.Lahiri K.Kashinath D. Tetrahedron 2002, 58: 9632 -
15d
Miyaura N. Advances in Metal-Organic Chemistry Vol. 6:Liebeskind LS. Jai Press; London: 1998. p.187 -
15e
Suzuki A. J. Organomet. Chem. 1997, 36: 2163 - 16
Kotha S.Tafesh A.Davenport K.Ortiz P. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2001, 40: 1166 - 17
Banerjee S. PhD Thesis Indian Institute of Technology Bombay; Mumbai: 2007. -
18a
Kaliappan KP.Subrahmanyam A.Palanichamy K. Chem. Eur. J. 2010, 8545 -
18b
Schreiber SL. Nature (London) 2009, 457: 153 -
18c
Mishra JKG.Panda G.
J. Comb. Chem. 2007, 9: 321 -
18d
Kotha S.Mandal K.Tiwari A.Mobin SM. Chem. Eur. J. 2006, 8024 -
18e
Burke MD.Berger EM.Schreiber SL. J. Am. Chem. Soc. 2004, 126: 14095 -
18f
Burke MD.Schreiber SL. Angew. Chem. Int. Ed. 2003, 43: 46 -
18g
Burke MD.Lalic G. Chem. Biol. 2002, 9: 535 -
18h
Schreiber SL.Nicolaou KC.Davies K. Chem. Biol. 2002, 9: 1 -
18i
Schreiber SL. Science 2000, 287: 1964