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Synlett 2009(19): 3135-3138
DOI: 10.1055/s-0029-1218293
DOI: 10.1055/s-0029-1218293
LETTER
© Georg Thieme Verlag
Stuttgart ˙ New York
Catalytic Intermolecular Hydroamination of Vinyl Ethers
Further Information
Received
30 July 2009
Publication Date:
21 October 2009 (online)
Publication History
Publication Date:
21 October 2009 (online)
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Abstract
This manuscript details the development of a palladium-catalyzed hydroamination of vinyl ethers. It is proposed that palladium catalyzes the hydroamination via Brønsted base catalysis, where palladium is protonated by the relatively acidic sulfonamide to generate a palladium hydride as well as the active anionic sulfonamide nucleophile. Thus, this process is distinct from known palladium-catalyzed hydroaminations of styrene derivatives that utilize less acidic amines.
Key words
hydroamination - vinyl ether - palladium - sulfonamide
-
1a
Mueller TE.Hultzsch KC.Yus M.Foubelo F.Tada M. Chem. Rev. 2008, 108: 3795 -
1b
Widenhoefer RA.Han X. Eur. J. Org. Chem. 2006, 4555 -
1c
Hazari N.Mountford P. Acc. Chem. Res. 2005, 38: 839 -
1d
Hultzsch KC. Org. Biomol. Chem. 2005, 3: 1819 -
1e
Hong S.Marks TJ. Acc. Chem. Res. 2004, 37: 673 -
1f
Mueller TE.Beller M. Chem. Rev. 1998, 98: 675 -
2a
Ohimiya H.Moriya T.Sawamura M. Org. Lett. 2009, 11: 2145 -
2b
Hesp KD.Stradiotto M. Org. Lett. 2009, 11: 1449 -
2c
Biyikal M.Lohnwitz K.Roesky PW.Bechert S. Synlett 2008, 3106 -
2d
Graebe K.Pohlki F.Doye S. Eur. J. Org. Chem. 2008, 4815 -
2e
Majumder S.Odom AL. Organometallics 2008, 27: 1174 -
2f
Liu Z.Hartwig JF. J. Am. Chem. Soc. 2008, 130: 1570 - For recent acid-catalyzed hydroaminations, see:
-
3a
Li Z.Zhang J.Brouwer C.Yang C.-G.Reich NW.He C. Org. Lett. 2006, 8: 4175 -
3b
Motokura K.Nakagiri N.Mori K.Mizugaki T.Ebitani K.Jitsukawa K.Kaneda K. Org. Lett. 2006, 8: 4617 -
3c
Rosenfeld DC.Shekhar S.Takemiya A.Utsunomiya M.Hartwig JF. Org. Lett. 2006, 8: 4179 -
3d
Schlummer B.Hartwig JF. Org. Lett. 2002, 4: 1471 -
3e
Colinas PA.Brave RD. Org. Lett. 2003, 5: 4509 -
3f
Toshima K.Nagai H.Ushiki Y.Matsumura S. Synlett 1998, 1007 -
3g
Karshtedt D.Bell AT.Tilly TD. J. Am. Chem. Soc. 2005, 127: 12640 -
3h
Widenhoefer R. Angew. Chem. Int. Ed. 2006, 45: 1747 -
3i
Jiao P.Nakashima D.Yamamoto H. Angew. Chem. Int. Ed. 2008, 47: 2411 -
4a
Kawatsura M.Hartwig JF. Organometallics 2001, 20: 1960 -
4b
Fadini L.Togni A. Chem. Commun. 2003, 30 -
4c
Li K.Hii KK. Chem. Commun. 2003, 1132 -
4d
Munro-Leighton C.Blue ED.Gunnoe TB. J. Am. Chem. Soc. 2006, 128: 1446 -
5a
Zhou J.Hartwig JF. J. Am. Chem. Soc. 2008, 130: 12220 -
5b
Giner X.Najera C. Org. Lett. 2008, 10: 2919 -
5c
Qin H.Yamagiwa N.Matsunaga S.Shibasaki M.
J. Am. Chem. Soc. 2006, 128: 1611 -
6a
Johns AM.Utsunomiya M.Incarvito CD.Hartwig JF. J. Am. Chem. Soc. 2006, 128: 1828 -
6b
Utsunomiya M.Hartwig JF. J. Am. Chem. Soc. 2003, 125: 14286 -
6c
Nettekoven U.Hartwig JF. J. Am. Chem. Soc. 2002, 124: 1166 -
6d
Kawatsura M.Hartwig JF. J. Am. Chem. Soc. 2000, 122: 9546 -
6e
Utsunomiya M.Hartwig JF.
J. Am. Chem. Soc. 2004, 126: 2702 -
6f
Utsunomiya M.Kuwano R.Motoi K.Hartwig JF. J. Am. Chem. Soc. 2003, 125: 5608 -
7a
Tada M.Shimamoto M.Sasaki T.Iwasawa Y. Chem. Commun. 2004, 2562 -
7b
Penzien J.Su RQ.Muller TE. J. Mol. Catal. A. 2002, 182-183: 489 -
7c
Vogels CM.Hayes PG.Shaver MP.Westcott SA. Chem. Commun. 2000, 51 - 8
Colinas PA.Bravo RD. Org. Lett. 2003, 5: 4509 - 9
Sherry BD.Loy RN.Toste FD. J. Am. Chem. Soc. 2004, 126: 4510 - 10
Cochran B.Michael FE. J. Am. Chem. Soc. 2008, 130: 2786 - 11
Shainyan BA.Grigor’eva AA. Russ. J. Org. Chem. 2001, 37: 1177 - 12
Knight JG.Ainge SW.Harm AM.Harwood SJ.Maughan HI.Armour DR.Hollinshead DM.Jaxa-Chamiec AA. J. Am. Chem. Soc. 2000, 122: 2944 - 13
Trost BM. Chem. Eur. J. 1998, 4: 2405 - 14
Luo S.Jordan RF. J. Am. Chem. Soc. 2006, 128: 12072