RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2002(12): 1675-1682
DOI: 10.1055/s-2002-33651
DOI: 10.1055/s-2002-33651
PAPER
© Georg Thieme Verlag Stuttgart · New York
Palladium-Catalyzed Sonogashira Coupling of 2,3-Dibromonorbornadiene: Synthesis of Symmetrical and Unsymmetrical Norbornadiene-2,3-diynes
Weitere Informationen
Received
23 April 2002
Publikationsdatum:
05. September 2002 (online)
Publikationsverlauf
Publikationsdatum:
05. September 2002 (online)
Abstract
Efficient syntheses of symmetrical (2 steps) and unsymmetrical (3 steps) norbornadiene-2,3-diynes 1 and 2 have been developed. Palladium-catalyzed Sonogashira coupling of 2,3-dibromonorbornadiene (8) with alkynes, using catalytic amount of Pd(PPh3)4, CuI, Et3N or BuNH2 in THF or toluene, provided symmetrical and unsymmetrical norbornadiene-2,3-diynes in good yields.
Key words
palladium - Sonogashira coupling - enediyne - norbornadiene
-
1a
Xi Z.Goldberg I. In Comprehensive Natural Products Chemistry Vol. 7:Barton DHR.Nakanishi K. Pergamon; Oxford: 1999. p.553 -
1b
Borders DB.Doyle TW. Enediyne Antibiotics as Antitumor Agents Marcel Dekker; New York: 1995. -
1c
Nicolaou KC.Smith AL. In Modern Acetylene ChemistryStang PJ.Diederich F. VCH; Weinheim: 1995. Chap. 7. - For reviews on enediyne cyclization, see:
-
2a
Wang KK. Chem. Rev. 1996, 96: 207 -
2b
Goldberg IH. Acc. Chem. Res. 1991, 24: 191 -
2c
Bergman RG. Acc. Chem. Res. 1973, 6: 25 - For recent studies of enediyne cyclizations, see:
-
3a
Jones LH.Harwig CW.Wentworth P.Simeonov A.Wentworth AD.Py S.Ashley JA.Lerner RA.Janda KD. J. Am. Chem. Soc. 2001, 123: 3607 -
3b
Rawat DS.Zaleski JM. J. Am. Chem. Soc. 2001, 123: 9675 - For recent examples of the synthesis of enediynes, see:
-
4a
Wandel H.Wiest O. J. Org. Chem. 2002, 67: 388 -
4b
Jones GB.Hynd G.Wright JM.Purohit A.Plourde GW.Huber RS.Mathews JE.Li A.Kilgore MW.Bubley GJ.Yancisin M.Brown MA. J. Org. Chem. 2001, 66: 3688 -
4c
König B.Pitsch W.Klein M.Vasold R.Prall M.Schreiner PR. J. Org. Chem. 2001, 66: 1742 -
4d
Jones GB.Wright JM.Plourde G.Purohit AD.Wyatt JK.Hynd G.Fouad F. J. Am. Chem Soc. 2000, 122: 9872 -
5a
Ryan JH.Stang PJ. J. Org. Chem. 1996, 61: 6162 -
5b
Stang PJ.Blume T.Zhdankin VV. Synthesis 1993, 35 - 6
Durr R.Cossu S.De Lucchi O. Synth. Commun. 1997, 27: 1369 - 7
Tranmer GK.Yip C.Handerson S.Jordan RW.Tam W. Can. J. Chem. 2000, 78: 527 -
8a
Tranmer GK.Tam W. J. Org. Chem. 2001, 66: 5113 -
8b
Tranmer GK.Keech P.Tam W. Chem. Commun. 2000, 863 -
9a
Yip C.Handerson S.Tranmer GK.Tam W. J. Org. Chem. 2001, 66: 276 -
9b
Yip C.Handerson S.Jordan R.Tam W. Org. Lett. 1999, 1: 791 - For reviews on Sonogashira coupling, see:
-
10a
Sonogashira K. In Metal-Catalyzed Cross-Coupling ReactionsDiederich F.Stang PJ. Wiley-VCH; London: 1998. p.203 -
10b
Sonogashira K. In Comprehensive Organic Synthesis Vol. 3:Trost BM.Fleming I. Pergamon; New York: 1991. p.521 - For recent developments on Sonogashira coupling, see:
-
11a
Radhakrishnan U.Stang PJ. Org. Lett. 2001, 3: 859 -
11b
Hundertmark T.Littke AF.Buchwald SL.Fu GC. Org. Lett. 2000, 2: 1729 -
11c
Thorand S.Krause N. J. Org. Chem. 1998, 63: 8551 - For examples on Glaser coupling of terminal acetylenes, see:
-
12a
Hoger S.Meckenstock A.-D.Pellen H. J. Org. Chem. 1997, 62: 4556 -
12b
de Meijere A.Kozhushkov S.Haumann T.Boese R.Puls C.Cooney MJ.Scott LT. Chem. Eur. J. 1995, 1: 124 -
12c
Boldi AM.Diederich F. Angew. Chem., Int. Ed. Engl. 1994, 33: 468 - 15
Still WC.Kahn M.Mitra A. J. Org. Chem. 1978, 43: 2923
References
For examples on the study of the effect of solvent in Sonogashira coupling, see Ref. [11c] and references cited therein.
14See Ref. [11c] and references cited therein.