A novel type of Pd/C-catalyzed hydrogenation using a catalyst poison: Chemoselective inhibition of the hydrogenolysis for O-benzyl protective group by the addition of a nitrogen-containing base

Tetrahedron

Volumn 54, Issue 46, 1998, Pages 13981-13996

  Sajiki, Hironao ^a   Hirota, Kosaku ^a  

^a GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; HYDROGENATION; PRIORITY JOURNAL;

EID: 0032512085     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00882-5     Document Type: Article

References (29)

1. 1 Part of this work was carried out at Metasyn, Inc. (current EPIX Medical, Inc.), 71 Rogers St., Cambridge, Massachusetts 02142, USA.
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8. 3, see: Bindra, J. S.; Grodski, A. J. Org. Chem. 1978, 16, 3240.
9. 5 While there has been only one reference about the selective inhibition of hydrogenolysis of aliphatic benzyl ether (11-benzyloxy-1-undecene) by the use of n-butylamine, the literature revealed no application to selective inhibition of other substrate; see: Czech, B. P.; Bartsh, R. A. J. Org. Chem. 1984, 49, 4077.
10. 6 The chemoselective hydrogenation of alkenes was recently reported without hydrogenolysis of the aliphatic O-benzyl groups by the use of the Lindlar catalyst, see: Ghosh, A. K.; Krishnan, K. Tetrahedron Lett. 1998, 39, 947.
11. 7 For preliminary communications, see: (a) Sajiki, H. Tetrahedron Lett. 1995, 36, 3465.
12. (b) Sajiki, H.; Kuno, H.; Hirota, K. Tetrahedron Lett. 1998, 39, 7127.
13. 8 The inhibitions of Pd/C-catalyzed hydrogenolysis of aliphatic O-benzyl ether with an amino group have been reported, for examples: (a) Sajiki, H.; Ong, K. Y.; Nadlar, S. T.; Wages, H. E.; McMurry, T. J. Synth. Commun. 1996, 26, 2511.
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16. 2, 0.5 equiv of pyridine, 24 h).
17. 10 Use of different suppliers [Aldrich, Acros, Kishida, Nakarai and N. E. Chemcat (former Engelhald)] did not cause differences in catalyst activity.
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20. 13 A similar over-reduction has been documented in the Rosenmund's reduction using a Pd catalyst with suitable catalyst poisons (modifiers), see: Maier, W. F.; Chettle, S. J.; Rai, R. S.; Thomas, G. J. Am. Chem. Soc. 1986, 108, 2608.
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23. 16 As 1,10-phenanthroline could be partially hydrogenated under the reaction conditions, 2,2'-dipyridyl was selected as an additive.
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