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Synlett 2007(11): 1675-1678
DOI: 10.1055/s-2007-984515
DOI: 10.1055/s-2007-984515
LETTER
© Georg Thieme Verlag Stuttgart · New York
Aerobic Ruthenium-Catalyzed Oxidative Transformation of Secondary Amines to Imines
Further Information
Received
10 April 2007
Publication Date:
25 June 2007 (online)
Publication History
Publication Date:
25 June 2007 (online)
Abstract
Aerobic, catalytic oxidation of secondary amines is performed efficiently in the presence of a diruthenium complex catalyst Ru2(OAc)4Cl to give the corresponding imines. The catalytic system is characterized by its high selectivity, activity, and operational simplicity.
Key words
ruthenium - oxidations - molecular oxygen - amines - imines
- 1
Murahashi S.-I. Angew. Chem., Int. Ed. Engl. 1995, 34: 2443 -
2a
Murahashi S.-I.Komiya N. Biomimetic Oxidations Catalyzed by Transition Metal ComplexesMunier B. Imperial College Press; London: 2000. p.563-611 -
2b
Murahashi S.-I.Imada Y. Transition Metals for Organic Synthesis 2nd ed., Vol 2: Wiley-VCH; Weinheim: 2004. p.497-507 - 3
Murahashi S.-I.Naota T.Taki H. J. Chem. Soc., Chem. Commun. 1985, 613 -
4a
Müller P.Gilabert DM. Tetrahedron 1988, 44: 7171 -
4b
Porta F.Crotti C.Cenini S.Palmisano G. J. Mol. Catal. 1989, 50: 333 - 5
Goti A.Romani M. Tetrahedron Lett. 1994, 35: 6567 - 6
Éll AH.Samec JSM.Brasse C.Bäckvall J.-E. Chem. Commun. 2002, 1144 - 7
Yamazaki S. Chem. Lett. 1992, 823 - 8
Choi H.Doyle MP. Chem. Commun. 2007, 745 -
9a
Anastas P.Warner JC. Green Chemistry: Theory and Practice Oxford University Press; Oxford: 1998. -
9b
Punniyamurthy T.Velusamy S.Iqbal J. Chem. Rev. 2005, 105: 2329 -
9c
Hill CL. Angew. Chem. Int. Ed. 2004, 43: 402 -
9d
Stahl SS. Angew. Chem. Int. Ed. 2004, 43: 3400 -
9e
Stahl SS. Science 2005, 309: 1824 -
9f
Thomas JM.Raja R. Catal. Today 2006, 117: 22 - 10
Tang R.Diamond SE.Neary N.Mares F. J. Chem. Soc., Chem. Commun. 1978, 562 - 11
Schröder M.Griffith WP. J. Chem. Soc., Chem. Commun. 1979, 58 - 12
Bailey AJ.James BR. Chem. Commun. 1996, 2343 -
13a
Griffith WP.Reddy B.Shoair AGF.Suriaatmaja M.White AJP.Williams DJ. J. Chem. Soc., Dalton Trans. 1998, 2819 -
13b
Griffith WP.Suriaatmaja M. Can. J. Chem. 2001, 79: 598 - 14
Mori K.Yamaguchi K.Mizugaki T.Ebitani K.Kaneda K. Chem. Commun. 2001, 461 - 15
Yamaguchi K.Mizuno N. Angew. Chem. Int. Ed. 2003, 42: 1480 - 16
Gao S.Herzig D.Wang B. Synthesis 2001, 544 - 17
Maeda Y.Nishimura T.Uemura S. Bull. Chem. Soc. Jpn. 2003, 76: 2399 - 18
Samec JSM.Éll AH.Bäckvall J.-E. Chem. Eur. J. 2005, 11: 2327 -
19a
Murahashi S.-I.Komiya N.Okano Y.Sato H. The 79th Annual Meeting of Chemical Society of Japan Kobe; Japan: 2001. Abstr. 1H306 -
19b
Murahashi S.-I,Komiya N, andOkano Y. inventors; JP 2002265430. - 20
Bloch R. Chem. Rev. 1998, 98: 1407 - 21 Ru2(OAc)4Cl was prepared from RuCl3 with AcOH, Ac2O, and LiCl according to the literature procedure. See:
Mitchell RW.Spencer A.Wilkinson G. J. Chem. Soc., Dalton Trans. 1973, 846 -
22a
Hosokawa T.Uno T.Inui S.Murahashi S.-I. J. Am. Chem. Soc. 1981, 103: 2318 -
22b
Hosokawa T.Murahashi S.-I. Acc. Chem. Res. 1990, 23: 49 - 23
Nishimura T.Onoue T.Ohe K.Uemura S. J. Org. Chem. 1999, 64: 6760 - 24
Murahashi S.-I.Komiya N.Terai H.Nakae T. J. Am. Chem. Soc. 2003, 125: 15312 - 25
Murahashi S.-I.Yoshimura N.Tsumiyama T.Kojima T. J. Am. Chem. Soc. 1983, 105: 5002