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-00000083.xml
Synlett 2012(2): 159-162
DOI: 10.1055/s-0031-1290117
DOI: 10.1055/s-0031-1290117
SYNPACTS
© Georg Thieme Verlag
Stuttgart ˙ New York
Oxidative Coupling of Tertiary Amines: Scope, Mechanism and Challenges
Further Information
Received
25 October 2011
Publication Date:
22 December 2011 (online)
Publication History
Publication Date:
22 December 2011 (online)
Abstract
This article highlights the current scope of oxidative coupling reactions of tertiary amines. Emphasis has been placed on recent synthetic and mechanistic studies and suggests potential areas of improvement for the future.
Key words
oxidation - cross-coupling - catalysis - mechanism - C-H functionalization
-
1a
Bergman RG. Nature (London) 2007, 446: 391 -
1b
Labinger JA.Bercaw JE. Nature (London) 2002, 417: 507 -
1c Readers are also directed
to the special ‘C-H Activation’ issue
of: Chem. Rev.
2010,
110:
575
-
2a
Colby DA.Bergman RG.Ellman JA. Chem. Rev. 2009, 110: 624 -
2b
Lyons TW.Sanford MS. Chem. Rev. 2010, 110: 1147 - 3
Zhenyang L. Coord. Chem. Rev. 2007, 251: 2280 - 4
Doyle MP.Duffy R.Ratnikov M.Zhou L. Chem. Rev. 2009, 110: 704 -
5a
Yeung CS.Dong VM. Chem. Rev. 2011, 111: 1215 -
5b
Scheuermann CJ. Chem. Eur. J. 2010, 5: 436 -
5c
Klussmann M.Sureshkumar D. Synthesis 2011, 353 -
6a
Murahashi S.-I.Komiya N.Terai H.Nakae T. J. Am. Chem. Soc. 2003, 125: 15312 -
6b
Murahashi S.-I.Komiya N.Terai H. Angew. Chem. Int. Ed. 2005, 44: 6931 -
6c
Murahashi S.-I.Nakae T.Terai H.Komiya N. J. Am. Chem. Soc. 2008, 130: 11005 - For earlier examples also, see:
-
7a
Santamaria J.Herlem D.Khuong-Huu F. Tetrahedron 1977, 33: 2389 -
7b
Chiba T.Takata Y. J. Org. Chem. 1977, 42: 2973 -
7c
Murata S.Teramoto K.Miura M.Nomura M. Bull. Chem. Soc. Jpn. 1993, 66: 1297 - 8
Li Z.Li C.-J. J. Am. Chem. Soc. 2005, 127: 6968 - 9
Li Z.Bohle DS.Li C.-J. Proc. Natl. Acad. Sci. U.S.A. 2006, 103: 8928 - 10
Li Z.Li C.-J. J. Am. Chem. Soc. 2004, 126: 11810 - 11
Li Z.Li C.-J. J. Am. Chem. Soc. 2005, 127: 3672 - 12
Li Z.Li C.-J. Eur. J. Org. Chem. 2005, 3173 -
13a
Li Z.Li C.-J. Org. Lett. 2004, 6: 4997 -
13b
Li Z.MacLeod PD.Li C.-J. Tetrahedron: Asymmetry 2006, 17: 590 - 14
Sureshkumar D.Sud A.Klussmann M. Synlett 2009, 1558 - 15
Boess E.Sureshkumar D.Sud A.Wirtz C.Farès C.Klussmann M. J. Am. Chem. Soc. 2011, 133: 8106 - 16
Condie AG.González-Gómez JC.Stephenson CRJ. J. Am. Chem. Soc. 2010, 132: 1464 - 17
Rueping M.Vila C.Koenigs RM.Poscharny K.Fabry DC. Chem. Commun. 2011, 47: 2360 - For additional photochemical methods, see:
-
18a
Hari DP.König B. Org. Lett. 2011, 13: 3852 -
18b
Pan Y.Wang S.Kee CW.Dubuisson E.Yang Y.Loh KP.Tan C.-H. Green Chem. 2011, DOI: 10.1039/C1GC15865A - 19
Zhao L.Li C.-J. Angew. Chem. Int. Ed. 2008, 47: 7075 - 20
Yang F.Li J.Xie J.Huang Z.-Z. Org. Lett. 2010, 12: 5214 - 21
Zhang G.Zhang Y.Wang R. Angew. Chem. Int. Ed. 2011, 50: 10429 - 22
Sundberg RJ.Théret M.-H.Wright L. Org. Prep. Proced. Int. 1994, 26: 386 - 23
Pandey G.Rani KS.Lakshmaiah G. Tetrahedron Lett. 1992, 33: 5107 - 24
Niu M.Yin Z.Fu H.Jiang Y.Zhao Y. J. Org. Chem. 2008, 73: 3961 - 25
Xu X.Li X. Org. Lett. 2009, 11: 1027 - 26
Daniels MH.Hubbs J. Tetrahedron Lett. 2011, 52: 3543 - 27
Ohta M.Quick MP.Yamaguchi J.Wünsch B.Itami K. Chem. Eur. J. 2009, 4: 1416 - 28
Kumaraswamy G.Murthy AN.Pitchaiah A. J. Org. Chem. 2010, 75: 3916 - 29
Chu L.Zhang X.Qing F.-L. Org. Lett. 2009, 11: 2197 -
30a
Chu L.Qing F.-L. Chem. Commun. 2010, 46: 6285 -
30b
Mitsudera H.Li C.-J. Tetrahedron Lett. 2011, 52: 1898 - 31
Sud A.Sureshkumar D.Klussmann M. Chem. Commun. 2009, 3169 - 32
Jones KM.Klussmann M. ChemCatChem 2011, in press; DOI: 10.1002/cctc.201100324 - 33
Ghobrial M.Schnürch M.Mihovilovic MD. J. Org. Chem. 2011, 76: 8781 - 34 An example of an iminium ion formed
in a metal-free procedure has been reported:
Tsang AS.-K.Jensen P.Hook JM.Hashmi ASK.Todd MH. Pure Appl. Chem. 2011, 83: 655
References
An example has been reported, see ref. 17.