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Synthesis 2001(13): 1932-1934
DOI: 10.1055/s-2001-17698
DOI: 10.1055/s-2001-17698
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Useful Benzocyclobutene Building Blocks via the Suzuki-Miyaura Coupling Reaction
Further Information
Received
22 May 2001
Publication Date:
10 August 2004 (online)
Publication History
Publication Date:
10 August 2004 (online)
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Abstract
A general and simple methodology for 3,6-diaryl benzocyclobutene (BCB) derivatives is reported using the Suzuki-Miyaura coupling reaction as a key step. Some of these building blocks are useful for the synthesis of a variety of BCB-based polymers.
Key words
boron - coupling - cycloadditions - polymers - palladium
-
1a
Michellys P.-Y.Pellissier H.Santelli M. Org. Prep. Proced. Int. 1996, 28: 545 -
1b
Sengura JL.Martin N. Chem. Rev. 1999, 99: 3199 -
1c
Mehta G.Kotha S. Tetrahedron 2001, 57: 625 -
2a
Kirchhoff RA.Bruza KJ. Chem. Tech. 1993, 22 -
2b
Kirchhoff RA.Bruza KJ. Adv. Polym. Sci. 1994, 117: 3 - 3
Hirsch A. Synthesis 1995, 895 and references cited therein - 4 WHO, Drug Information 1996, 10: 102
-
5a
Skorcz JA. inventors; US Patent 3, 408391. -
5c For BCB-based a-amino acids synthesis, see:
Kotha S.Sreenivasachary N.Halder S. Bioorg. Med. Chem. Lett. 1999, 9: 2565 - For recent examples in BCB polymers:
-
6a
Tan L.-S.Arnold FE. J. Polym. Sci., Part A: Polym. Chem. 1988, 26: 1819 -
6b
Hahn SF.Martin SJ.Mckelvy ML.Patrick DW. Macromolecules 1993, 26: 3870 -
6c
Deeter GA.Venkataraman D.Kampf JW.Moore JS. Macromolecules 1994, 27: 2647 -
6d
DeLassus SL.Howell BA. Macromolecules 1994, 27: 1307 -
6e
Marks MJ.Erskine JS.McCrery DA. Macromolecules 1994, 27: 4117 -
6f
Chino K.Takata T.Endo T. Macromolecules 1995, 28: 5947 -
7a
Stanforth SP. Tetrahedron 1998, 54: 263 -
7b
Miyaura N.Suzuki A. Chem. Rev. 1995, 95: 2457 -
7c
Martin AR.Yang Y. Acta Chem. Scand. 1993, 47: 221 -
7d
Miyaura N. In Advances in Metal-organic Chemistry Vol. 6: Jai Press; Connecticut: 1998. p.187-243 - 9
Walker KA.Markoski LJ.Moore JS. Synthesis 1992, 1265 - 10
Bennetau B.Dunogues J. Synlett 1993, 171 -
11a
O’Donovan ARM.Shepherd MK. Tetrahedron Lett. 1994, 35: 4425 -
11b
Simpkins NS. Sulphones In Organic Synthesis Pergamon Press; New York: 1993. - For recent examples on conjugated polymers, see:
-
12a
Conjugated Polymers and Related Materials, Salaneck WR.Lundstrom I.Ranby B. Oxford University Press; Oxford: 1993. -
12b
Halls JJM.Walsh CA.Greenham NC.Marseglia EA.Friend RH.Moratti SC.Holmes AB. Nature 1995, 376: 498 -
12c
Greenham NC.Moratti SC.Bardley DDC.Friend RH.Holmes AB. Nature 1993, 365: 628 -
12d
Granier F.Hajlaoui R.Yassar A.Srivastava P. Science 1994, 265: 1684 -
12e
Kaeriyama K. In Handbook of Organic Conductive Molecules and Polymers Vol. 2:Nalwa HS. Wiley; New York: 1997. p.271 - 13
Coulson DR. Inorg. Synth. 1972, 13: 121 - 14
Brandsma L.Vasilevsky SF.Verkruijsse HS. Application of Transition Metal Catalyst in Organic Synthesis Springer; Berlin: 1998. p.13
References
A portion of the work has been presented: Kotha, S.; Chakraborty, K.; Ganesh, T.; Halder, S.; Sreenivasachary, N. Boronic Acids in Organic Synthesis, Presented at the 2nd National Symposium in Chemistry, IICT, Hyderabad, January 2000