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Synthesis 2004(15): 2527-2534
DOI: 10.1055/s-2004-831205
DOI: 10.1055/s-2004-831205
PAPER
© Georg Thieme Verlag Stuttgart · New York
Novel Synthetic Strategy of N-Arylated Heterocycles via Sequential Palladium-Catalyzed Intra- and Inter-Arylamination Reactions
Further Information
Received
19 May 2004
Publication Date:
02 September 2004 (online)
Publication History
Publication Date:
02 September 2004 (online)
Abstract
The use of an in situ generated Pd(0) catalyst associated to N,N′-bis(2,6-diisopropylphenyl)dihydroimidazol-2-ylidene (SIPr) as a ligand and t-BuONa as the base for sequential intra- followed by intermolecular aryl amination is described. The method has been applied to the synthesis of N-arylated five-, six- and seven-membered nitrogen heterocycles.
Key words
palladium catalyst - N-heterocyclic carbene ligand - aryl amination reaction - N-arylated heterocycles
-
1a
Combs DW.Rampulla MS.Bell SC.Klaubert DH.Tobia AJ.Falotico R.Haertlein B.Lakas-Weiss C.Moore JB. J. Med. Chem. 1990, 33: 380 -
1b
Stabler SR. ; Jahangir Synth. Commun. 1994, 24: 123 -
1c
Andersen K.Liljefors T.Hyttel J.Perregaard J. J. Med. Chem. 1996, 39: 3723 -
1d
Spadoni G.Balsamini C.Bedini A.Diamantini G.Giancomo BD.Tontini A.Tarzia G. J. Med. Chem. 1998, 41: 3624 -
1e
Abramov IG.Smirnov AV.Kalandadza LS.Sakharov VN.Plakhtinskii VV. Heterocycles 2003, 60: 1611 - For reviews, see:
-
2a
Wolfe JP.Wagaw S.Marcoux J.-F.Buchwald SL. Acc. Chem. Res. 1998, 31: 805 -
2b
Hartwig JF. Angew. Chem. Int. Ed. 1998, 37: 2046 -
2c
Yang BH.Buchwald SL. J. Organomet. Chem. 1999, 576: 125 -
2d
Muci AR.Buchwald SL. Practical Palladium Catalysts for C-N and C-O Bond Formation, In Cross-Coupling Reaction: A Practical Guide, Topics in Current Chemistry Ser. 219Miyaura N. Springer-Verlag; New York: 2002. -
3a
Wolfe JP.Buchwald SL. J. Am. Chem. Soc. 1997, 119: 6054 -
3b
Brenner E.Fort Y. Tetrahedron Lett. 1998, 39: 5359 -
3c
Brenner E.Schneider R.Fort Y. Tetrahedron 1999, 55: 12829 -
3d
Desmarets C.Schneider R.Fort Y. Tetrahedron Lett. 2000, 41: 2875 -
3e
Brenner E.Schneider R.Fort Y. Tetrahedron Lett. 2000, 41: 288 -
3f
Lipshutz BH.Ueda H. Angew. Chem. Int. Ed. 2000, 39: 4492 -
3g
Desmarets C.Schneider R.Fort Y. Tetrahedron Lett. 2001, 42: 247 -
3h
Desmarets C.Schneider R.Fort Y. Tetrahedron 2001, 57: 7657 -
3i
Brenner E.Schneider R.Fort Y. Tetrahedron 2002, 58: 6913 -
3j
Desmarets C.Schneider R.Fort Y.Walcarius A. J. Chem. Soc., Perkin Trans. 2 2002, 1844 -
3k
Lipshutz BH.Tasler S.Chrisman W.Spliethoff B.Tesche B. J. Org. Chem. 2003, 68: 1177 -
3l
Tasler S.Lipshutz BH. J. Org. Chem. 2003, 68: 1190 -
4a
Wolfe JP.Rennels RA.Buchwald SL. Tetrahedron 1996, 52: 7525 -
4b
Peat AJ.Buchwald SL. J. Am. Chem. Soc. 1996, 118: 1028 -
4c
Wagaw S.Rennels RA.Buchwald SL. J. Am. Chem. Soc. 1997, 119: 8451 -
4d
He F.Foxman BM.Snider BB. J. Am. Chem. Soc. 1998, 120: 6417 -
4e
Abouabdellah A.Dodd RH. Tetrahedron Lett. 1998, 39: 2119 -
4f
Yang BH.Buchwald SL. Org. Lett. 1999, 1: 35 -
4g
Watanabe M.Yamamoto T.Nishiyama M. Angew. Chem. Int. Ed. 2000, 39: 2501 -
4h
Brown JA. Tetrahedron Lett. 2000, 41: 1623 -
4i
Song JJ.Yee NK. Org. Lett. 2000, 2: 519 -
4j
Song JJ.Yee NK. Tetrahedron Lett. 2001, 42: 2937 -
4k
Yu Y.Ostrech JM.Houghten RA. Tetrahedron Lett. 2003, 44: 2569 -
4l
Qadir M.Priestley RE.Rising TWD.Gelbrich T.Coles SM.Hursthouse MB.Sheldrake PW.Whittall N.Hii KK. Tetrahedron Lett. 2003, 44: 3675 -
4m
Brain CT.Steer JT. J. Org. Chem. 2003, 68: 6814 -
5a
Hartwig JF.Kawatsura M.Hauck SI.Shaughnessy KH.Alcazar-Roman LM. J. Org. Chem. 1999, 64: 5575 -
5b
Old DW.Harris MC.Buchwald SL. Org. Lett. 2000, 2: 1403 -
5c
Meneyrol J.Helissey P.Tratrat C.Giorgi-Renault S.Husson H.-P. Synth. Commun. 2001, 31: 987 -
6a
Beller M.Breindl C.Riermeier TH.Eichberger M.Trauthwein H. Angew. Chem. Int. Ed. 1998, 37: 3389 -
6b
Beller M.Breindl C.Riermeier TH.Tillack A. J. Org. Chem. 2001, 66: 1403 -
7a
Herrmann WA.Reisinger CP.Spiegler M. J. Organomet. Chem. 1998, 557: 93 -
7b
Böhm VPW.Gstöttmayr CWK.Weskamp T.Herrmann WA. J. Organomet. Chem. 2000, 595: 186 -
7c
Bourissou D.Guerret O.Gabbaï FP.Bertrand G. Chem. Rev. 2000, 100: 39 -
7d
Herrmann WA. Angew. Chem. Int. Ed. 2002, 41: 1290 -
8a
Gradel B.Brenner E.Schneider R.Fort Y. Tetrahedron Lett. 2001, 42: 5689 -
8b
Desmarets C.Schneider R.Fort Y. J. Org. Chem. 2002, 67: 3029 - 9
Omar-Amrani R.Thomas A.Brenner E.Schneider R.Fort Y. Org. Lett. 2003, 5: 2311 -
10a
Desmarets C.Kuhl S.Schneider R.Fort Y. Organometallics 2002, 21: 1554 -
10b
Kuhl S.Schneider R.Fort Y. Adv. Synth. Catal. 2003, 345: 341 -
10c
Kuhl S.Schneider R.Fort Y. Organometallics 2003, 22: 4184 -
11a
Huang J.Grasa G.Nolan SP. Org. Lett. 1999, 1: 1307 -
11b
Grasa GA.Viciu MS.Huang J.Nolan SP. J. Org. Chem. 2001, 66: 7729 -
11c
Viciu MS.Kissling RM.Stevens ED.Nolan SP. Org. Lett. 2002, 4: 2229 -
11d
Hillier AC.Grasa GA.Viciu MS.Lee HM.Yang C.Nolan SP. J. Organomet. Chem. 2002, 653: 69 -
11e
Viciu MS.Kelly RA.Stevens ED.Naud F.Studer M.Nolan SP. Org. Lett. 2003, 5: 1479 -
11f
Marion N.Navarro O.Kelly RA.Nolan SP. Synthesis 2003, 2590 - 12
Stauffer SR.Lee S.Stambuli JP.Hauck SI.Hartwig JF. Org. Lett. 2000, 2: 1423 -
13a
Selvakumar K.Zapf A.Spannenberg M.Beller M. Chem.-Eur. J. 2002, 8: 3901 -
13b
Selvakumar K.Zapf A.Beller M. Org. Lett. 2002, 4: 3031 -
13c
Jackstell R.Frisch A.Beller M.Röttger D.Malaun M.Bildstein B. J. Mol. Catal. A: Chem. 2002, 185: 105 -
13d
Frisch AC.Zapf A.Briel O.Kayser B.Shaikh N.Beller M. J. Mol. Cat. A: Chem. 2004, 214: 231 -
14a
Böhm VPW.Weskamp T.Gstöttmayr CWK.Herrmann WA. Angew. Chem. Int. Ed. 2000, 39: 1602 -
14b
Böhm VPW.Gstöttmayr CWK.Weskamp T.Herrmann WA. Angew. Chem. Int. Ed. 2001, 40: 3387 -
14c
Herrmann WA.Olefe K.Von Preysing D.Schneider SK. J. Organomet. Chem. 2003, 687: 229 - 16
Perrin DD.Amarego WLF. Purification of Laboratory Chemicals 3rd ed.: Pergamon; Oxford: 1998.
References
SIPr·HCl is commercially available from Strem Chemicals Inc.