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Synthesis 2007(21): 3329-3332
DOI: 10.1055/s-2007-990804
DOI: 10.1055/s-2007-990804
PAPER
© Georg Thieme Verlag Stuttgart · New York
Cobalt(III) Complex Catalyzed Aerobic Oxidation of Propargylic Alcohols
Further Information
Received
2 August 2007
Publication Date:
21 September 2007 (online)
Publication History
Publication Date:
21 September 2007 (online)
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Abstract
An o-phenylenebis(N′-methyloxamidate) cobalt(III) complex works as an efficient catalyst for the oxidation of propargylic alcohols to the corresponding α,β-acetylenic carbonyl compounds, in the presence of pivalaldehyde, under an atmospheric pressure of molecular oxygen.
Key words
alcohols - alkynes - cobalt complexes - oxidation - homogeneous catalysis - oxygen
- 1
Adlington RM.Baldwin JE.Pritchard GJ.Spencer KC. Tetrahedron Lett. 2000, 41: 575 - 2
Kundu NG.Mahanty JS.Spears CP. Bioorg. Med. Chem. Lett. 1996, 6: 1497 - 3
Clennan EL.Heah PC. J. Org. Chem. 1981, 46: 4107 - 4
Aiguade J.Hao J.Forsyth CJ. Org. Lett. 2001, 3: 979 - 5
Alonso DA.Nájera C.Pacheco MC. J. Org. Chem. 2004, 69: 1615 ; and references cited therein - 6
Zhang X.Sarkar S.Larock RC. J. Org. Chem. 2006, 71: 236 -
7a
Bishop BC.Brands KMJ.Gibb AD.Kennedy DJ. Synthesis 2004, 53 -
7b
Waldo JP.Larock RC. Org. Lett. 2005, 7: 5203 -
7c
Zhou C.Dubrovsky AV.Larock RC. J. Org. Chem. 2006, 71: 1626 -
7d
Tseng J.-C.Chen J.-H.Luh T.-Y. Synlett 2006, 1209 -
7e
Bagley MC.Lubinu MC.Mason CJ. Synlett 2007, 704 -
8a
Wang B.Bonin M.Micouin L. Org. Lett. 2004, 6: 3481 -
8b
Wang B.Bonin M.Micouin L. J. Org. Chem. 2005, 70: 6126 -
8c
Stefani HA.Cella R.Dörr FA.de Pereira CMP.Gomes FP.Zeni G. Tetrahedron Lett. 2005, 46: 2001 -
9a
Nielsen TE.Cubillo de Dios MA.Tanner D. J. Org. Chem. 2002, 67: 7309 -
9b
Chen L.Li C.-J. Org. Lett. 2004, 6: 3151 -
9c
Oh CH.Reddy VR. Tetrahedron Lett. 2004, 45: 8545 -
9d
Cox RJ.Ritson DJ.Dane TA.Berge J.Charmant JPH.Kantacha A. Chem. Commun. 2005, 1037 -
9e
Palimkar SS.Kumar PH.Jogdand NR.Daniel T.Lahoti RJ.Srinivasan KV. Tetrahedron Lett. 2006, 47: 5527 -
10a
Ahmed MSM.Mori A. Org. Lett. 2003, 5: 3057 -
10b
Sans V.Trzeciak AM.Luis S.Ziolkowski JJ. Catal. Lett. 2006, 109: 37 -
10c
Rahman MT.Fukuyama T.Kamata N.Sato M.Ryu I. Chem. Commun. 2006, 2236 - 11
Sakai N.Kanada R.Hirasawa M.Konakahara T. Tetrahedron 2005, 61: 9298 -
12a
Chernick ET.Eisler S.Tykwinski RR. Tetrahedron Lett. 2001, 42: 8575 -
12b
Shun ALKS.Chernick ET.Eisler S.Tykwinski RR. J. Org. Chem. 2003, 68: 1339 -
12c
Lin C.-F.Lu W.-D.Wang I.-W.Wu M.-J. Synlett 2003, 2057 - 13
Ley SV.Madin A. In Comprehensive Organic Synthesis Vol. 7:Trost BM.Fleming I. Pergamon Press; New York: 1991. p.251 -
14a
Frontiers in Benign Chemical Syntheses and Processes
Anastas PT.Williamson TC. Oxford University Press; Oxford: 1998. -
14b
Anastas PT.Kirchhoff MM. Acc. Chem. Res. 2002, 35: 686 -
15a
Maeda Y.Kakiuchi N.Matsumura S.Nishimura T.Uemura S. Tetrahedron Lett. 2001, 42: 8877 -
15b
Maeda Y.Kakiuchi N.Matsumura S.Nishimura T.Kawamura T.Uemura S. J. Org. Chem. 2002, 67: 6718 - 16
Maeda Y.Washitake Y.Nishimura T.Iwai K.Yamauchi T.Uemura S. Tetrahedron 2004, 60: 9031 - 17
Sakaguchi S.Takase T.Iwahara T.Ishii Y. Chem. Commun. 1998, 2037 - 18
Masutani K.Uchida T.Irie R.Katsuki T. Tetrahedron Lett. 2000, 41: 5119 - 19
Sharma VB.Jain SL.Sain B. Tetrahedron Lett. 2003, 44: 383 - 20
Radosevich AT.Musich C.Toste FD. J. Am. Chem. Soc. 2005, 127: 1090 -
21a
Fernández I.Pedro JR.Roselló AL.Ruiz R.Castro I.Ottenwaelder X.Journaux Y. Eur. J. Org. Chem. 2001, 1235 -
21b
Blay G.Fernández I.Marco-Aleixandre A.Monje B.Pedro JR.Ruiz R. Tetrahedron 2002, 58: 8565 -
21c
Barroso S.Blay G.Cardona L.Fernández I.García B.Pedro JR. J. Org. Chem. 2004, 69: 6821 -
21d
Blay G.Fernández I.Monje B.Pedro JR. Tetrahedron Lett. 2004, 45: 8039 -
21e
Barroso S.Blay G.Fernández I.Pedro JR.Ruiz .Pardo E.Lloret F.Muñoz MC. J. Mol. Catal. A: Chem. 2006, 243: 214 -
22a
Mukaiyama T. Bull. Chem. Soc. Jpn. 1995, 68: 17 -
22b
Mukaiyama T. Aldrichimica Acta 1996, 29: 59 - 23
Gao G.Xie R.-G.Pu L. Proc. Natl. Acad. Sci. U.S.A. 2004, 101: 5417 - 24
Yamaguchi M.Shibato K.Fujiwara S.Hirao I. Synthesis 1986, 421 - 25
Uenoyama Y.Fukuyama T.Morimoto K.Nobuta O.Nagai H.Ryu I. Helv. Chim. Acta 2006, 89: 2483