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(8): 1281-1289
DOI: 10.1055/s-2004-822354
DOI: 10.1055/s-2004-822354
PAPER
© Georg Thieme Verlag Stuttgart · New York
Palladium-Tetraphosphine Complex: An Efficient Catalyst for the Alkynylation of ortho-Substituted Aryl Bromides
Further Information
Received
17 March 2004
Publication Date:
03 May 2004 (online)
Publication History
Publication Date:
03 May 2004 (online)
Abstract
The tetraphosphine cis,cis,cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane in combination with [Pd(C3H5)Cl]2 affords a very efficient catalyst for the alkynylation of ortho-substituted aryl bromides. A wide variety of substituents such as phenyl, trifluoromethyl, acetyl, formyl or nitrile, are tolerated. High turnover numbers can be obtained with most of these aryl bromides. The coupling of sterically very congested aryl bromides such as 9-bromoanthracene or 2,4,6-triisopropylbromobenzene also proceeds in good yields.
Key words
palladium - tetraphosphine - catalysis - alkynylation - alkynes - aryl bromides
- For reviews on the Pd-catalysed reaction of aryl halides with alkynes see:
-
1a
Sonogashira K. Metal-Catalyzed Cross-Coupling ReactionsDiederich F.Stang PJ. Wiley-VCH; New York: 1998. -
1b
Brandsma L.Vasilevsky SF.Verkruijsse HD. Application of Transition Metal Catalysts in Organic Synthesis Springer-Verlag; Berlin: 1998. -
1c
Sonogashira K. J. Organomet. Chem. 2002, 653: 46 - For examples of efficient Pd-catalysts for the alkynylation of aryl halides:
-
2a
Herrmann WA.Reisinger C.-P.Spiegler M. J. Organomet. Chem. 1998, 557: 93 -
2b
Nakamura K.Okubo H.Yamaguchi M. Synlett 1999, 549 -
2c
Herrmann WA.Böhm V.Reisinger C.-P. J. Organomet. Chem. 1999, 576: 23 -
2d
McGuinness D.Cavell K. Organometallics 2000, 19: 741 -
2e
Buchmeiser M.Schareina T.Kempe R.Wurst K. J. Organomet. Chem. 2001, 634: 39 -
2f
Batey RA.Shen M.Lough AJ. Org. Lett. 2002, 4: 1411 -
2g
Yang C.Nolan S. Organometallics 2002, 21: 1020 -
2h
Méry D.Heuzé K.Astruc D. Chem. Commun. 2003, 1934 - For selected examples of Pd-catalysed reaction of ortho-substituted aryl halides with alkynes using PPh3 as ligand:
-
3a
Kondo Y.Shiga F.Murata N.Sakamoto T.Yamanaka H. Tetrahedron 1994, 50: 11803 -
3b
Makra F.Rohloff JC.Muehldorf AV.Link JO. Tetrahedron Lett. 1995, 46: 6815 -
3c
Bleicher LS.Cosford NDP.Herbaut A.McCallum JS.McDonald IA. J. Org. Chem. 1998, 63: 1109 -
3d
Pschirer NG.Bunz UHF. Tetrahedron Lett. 1999, 40: 2481 -
3e
Dyker G.Stirner W.Henkel G. Eur. J. Org. Chem. 2000, 1433 -
3f
Kabalka GW.Wang L.Namboodiri V.Pagni RM. Tetrahedron Lett. 2000, 41: 5151 -
3g
Hiroya K.Jouka R.Kameda M.Yasuhara A.Sakamoto T. Tetrahedron 2001, 57: 9697 -
3h
Mori A.Shimada T.Kondo T.Sekiguchi A. Synlett 2001, 649 -
3i
Kabalka GW.Wang L.Pagni RM. Tetrahedron 2001, 57: 8017 -
3j
Roesch KR.Larock RC. J. Org. Chem. 2002, 67: 86 -
3k
Huang Q.Hunter JA.Larock RC. J. Org. Chem. 2002, 67: 3437 -
3l
Koradin C.Dohle W.Rodriguez AL.Schmid B.Knochel P. Tetrahedron 2003, 59: 1571 - 4
Böhm VPW.Herrmann WA. Eur. J. Org. Chem. 2000, 3679 - 5
Hundertmark T.Littke A.Buchwald S.Fu G. Org. Lett. 2000, 2: 1729 - 6
Köllhofer A.Pullmann T.Plenio H. Angew. Chem. Int. Ed. 2003, 42: 1056 - 7
Alonso D.Najera C.Pacheco C. Tetrahedron Lett. 2002, 43: 9365 - 8
Köllhofer A.Plenio H. Chem.-Eur. J. 2003, 9: 1416 - 9
Laurenti D.Feuerstein M.Pèpe G.Doucet H.Santelli M. J. Org. Chem. 2001, 66: 1633 - 10
Feuerstein M.Laurenti D.Bougeant C.Doucet H.Santelli M. Chem. Commun. 2001, 325 - 11
Feuerstein M.Doucet H.Santelli M. J. Org. Chem. 2001, 66: 5923 -
12a
Feuerstein M.Berthiol F.Doucet H.Santelli M. Org. Biomol. Chem. 2003, 1: 2235 -
12b
Feuerstein M.Doucet H.Santelli M. Tetrahedron Lett. 2004, 45: 1630 - 13
Amatore C.Bensalem S.Ghalem S.Jutand A.Medjour Y. Eur. J. Org. Chem. 2004, 366 - 14
Kamikawa T.Hayashi T. J. Org. Chem. 1998, 63: 8922 - 15
Littke AF.Schwarz L.Fu GC. J. Am. Chem. Soc. 2002, 124: 6343 - 16
Shirakawa E.Hoshida H.Takaya H. Tetrahedron Lett. 1997, 38: 3759 - 17
Barluenga J.Vazquez-Villa H.Ballesteros A.Gonzalez JM. J. Am. Chem. Soc. 2003, 125: 9028 - 18
Wadsworth DH.Donatelli BA. Synthesis 1981, 285 - 19
Castanet A.-S.Colobert F.Schlama T. Org. Lett. 2000, 2: 3559 - 20
Dehmlow EV.Winterfeldt A. Z. Naturforsch. B: Chem. Sci. 1989, 44: 455 - 21
Liron F.LeGarrec P.Alami M. Synlett 1999, 246 - 22
Uemoto K,Koide T,Uchihori T,Yamada S, andKojo K. inventors; Jpn. Patent, JP 10182636. ; Chem. Abstr. 1998 , 129, 144875 - 23
Zeller M, andJeanguenat A. inventors; PCT Int. Appl., WO 9907674. ; Chem. Abstr. 1999, 130, 196950 - 24
Prestwich GD.Eng W.Deaton E.Wichern D. J. Chem. Ecol. 1984, 10: 1201 - 25
Lee GCM.Syage ET.Harcourt DA.Holmes JM.Garst ME. J. Org. Chem. 1991, 56: 7007