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-00000084.xml
Synthesis 2004(4): 549-557
DOI: 10.1055/s-2004-815981
DOI: 10.1055/s-2004-815981
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Symmetrical and Unsymmetrical 9,10-Diarylanthracene Derivatives via Bis-Suzuki-Miyaura Cross-Coupling Reaction
Further Information
Received
11 September 2003
Publication Date:
19 February 2004 (online)
Publication History
Publication Date:
19 February 2004 (online)
Abstract
Synthesis of various 9,10-diarylanthracene derivatives via bis-Suzuki-Miyaura cross-coupling reaction as a key step is described. Availability of the 9,10-dithienylanthracenes derivatives where the thiophene unit is present in the molecule (e. g. 11, 12, 14) may provide an easy access to novel polymer and/or dendrimer preparation. In addition, we have synthesized unsymmetrical 9,10-diarylanthracene derivatives 20-25 by the Suzuki-Miyaura cross-coupling reaction, which are difficult to prepare by other transition metal-catalyzed cross-coupling reactions.
Key words
arenes - boron - coupling - palladium - polymers
- 1
Marcus RA. Angew. Chem., Int. Ed. Engl. 1993, 32: 1111 - 2
Paddon-Row MN. Acc. Chem. Res. 1994, 27: 18 - 3
Huber R. Angew. Chem., Int. Ed. Engl. 1989, 28: 848 - 4
Deisenhofer J.Michel H. Angew. Chem., Int. Ed. Engl. 1989, 28: 829 - 5
Williams DJ. Angew. Chem., Int. Ed. Engl. 1984, 23: 690 - 6
Kanis DR.Ratner MA.Mark TJ. J. Am. Chem. Soc. 1992, 114: 10338 - 7
Kaino T.Tomaru S. Adv. Mater. 1993, 5: 172 - 8
Grätzel M.Kalyanasundaram K. Curr. Sci. 1994, 66: 706 - 9
Babu KSC.Srivasta ON.Rao GVS. Curr. Sci. 1994, 66: 715 - 10
Nalwa HS.Kakuta A. Appl. Organomet. Chem. 1992, 6: 645 - 11
Wagner G.Herrmann R.Scherer W. J. Organomet. Chem. 1996, 516: 225 - 12
Yee WA.Kuzmin VA.Kliger DS.Hammond GS.Twarowski AJ. J. Am. Chem. Soc. 1979, 101: 5104 - 13
Liu DKK.Faulkner LR. J. Am. Chem. Soc. 1977, 99: 4594 - 14
Wilson T. J. Am. Chem. Soc. 1969, 91: 2387 - 15
Engstrom RC.Johnson KW.Desjarlais S. Anal. Chem. 1987, 59: 670 - 16
Molay JT.Bard AJ. J. Am. Chem. Soc. 1971, 93: 5968 - 17
Maricle DL.Maurer A. J. Am. Chem. Soc. 1967, 89: 188 - 18
Adam W.Cueto O.Yany F. J. Am. Chem. Soc. 1978, 100: 2587 - 19
Adam W.Cancio EM.Rodriguez O. Photochem. Photobiol. 1978, 27: 617 - 20
Romanets RG.Prock A.Zahradnik R. J. Phys. Chem. 1970, 53: 4093 - 21
Herkstroeter WG.Merkel PB. J. Photochem. 1981, 16: 331 -
22a
Smet M.Dijk JV.Dehanen W. Synlett 1999, 495 -
22b
Smet M.Dijk JV.Dehanen W. Tetrahedron 1999, 55: 7859 ; and references cited therein - 23
Kotha S.Ghosh AK.Behera M. Indian J. Chem., Sect. B 2002, 41: 2330 - 24
Ingold KC.Marshall GP. J. Chem. Soc. 1926, 3080 - 25
Willmart A. Bull. Soc. Chim. Fr. 1942, 9: 83 - 26
Etienne A.Arditti G.Chmelevsky A. Bull. Soc. Chim. Fr. 1965, 669 - 27
Blank DH.Gribble GW. Tetrahedron Lett. 1997, 38: 4761 - 28
Kauffman JM. Synthesis 2001, 197 - 29
Goossens R.Smet M.Dehanen W. Tetrahedron Lett. 2002, 43: 6605 - 30
Zeng B.-b.King SB. Synthesis 2002, 2335 - 31
Pai J.Yu W.-L.Ni J.Lai Y.-H.Huang W.Heerger AJ. Macromolecules 2001, 34: 7241 - 32
Gigli AW.Barbarella G.Favaretto L.Cacialli F.Cingolani R. Appl. Phys. Lett. 1999, 75: 439 - 33
Granlund T.Theander M.Bergreen M.Anderson MR.Ruzeckas A.Sundstrom V.Bjork G.Granstrom M.Inganas O. Chem. Phys. Lett. 1998, 288: 879 - 34
van Mullekom HAM. Ph.D. Thesis Eindhoven University of Technology; The Netherlands: 2000. - 35
Cooke A.Wagener KB. Macromolecules 1991, 26: 2704 - 36
Iwatsuki S.Kubo M.Ito Y. Chem. Lett. 1993, 1085 - 37
Cornelissen JJLM.Peeters E.Jansen RJ.Meijer EW. Acta Polym. 1998, 49: 476 - 38
Kim K.-K,Son S.-H,Yoon S.-H,Bae J.-S,Lee Y.-G,Im S.-G,Kim J.-E, andLee J.-C. inventors; WO 2002O88274. ; Chem. Abstr. 2002, 137, 360139 - 39
Azuma H,Hosokawa C, andKusumoto T. inventors; Japanese Patent 200053676. ; Chem. Abstr. 2000, 132, 173450 - 40
Miyaura N.Yanagi T.Suzuki A. Synth. Commun. 1981, 513 - 41
Martin AR.Yang Y. Acta. Chem. Scand. 1993, 47: 221 -
42a
Suzuki A. Pure Appl. Chem. 1994, 66: 213 -
42b
Miyaura N.Suzuki A. Chem. Rev. 1995, 95: 2457 -
43a
Tanaka K.Endo K.Aoyama Y. Chem. Lett. 1999, 887 -
43b
Brownstein SK.Ding J.Robertson G.Roovers J. J. Org. Chem. 2002, 67: 663 - 44
Stanforth SP. Tetrahedron 1998, 54: 263 - 45
Suzuki A. J. Organomet. Chem. 1999, 576: 147 - 46
Kotha S.Lahiri K.Kasinath D. Tetrahedron 2002, 58: 9633 - 47
Kotha S.Ghosh AK. Synlett 2002, 451 - 48
Balaganesan B.Sen WJ.Chen CH. Tetrahedron Lett. 2003, 44: 5747 - 49
Jones SJ.Atherton CC. Synth. Commun. 2001, 31: 1799 - 50 Aldrich Handbook of Fine Chemicals and Laboratory Equipment 2003-2004 Aldrich; Milwaukee: 2003. Cat. No. 26930-1. p.230
-
51a
Coulson DR. Inorg. Synth. 1972, 13: 121 -
51b
Brandsma L.Vasilevsky SF.Verkruijsse HS. Application of Transition Metal Catalyst in Organic Synthesis Springer; Berlin: 1998. p.13 - 52
Teki Y.Miyamoto S.Nakatsuji M.Miura Y. J. Am. Chem. Soc. 2001, 123: 294