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
References
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
5a Skorcz JA. inventors; US Patent 3, 408391.
5c 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
8 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
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.
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
