Highly chemoselective hydrogenation method using novel finely dispersed palladium catalyst on silk-fibroin: its preparation and activity

A palladium–fibroin complex (Pd/Fib) was prepared by soaking silk-fibroin in MeOH solution of Pd(OAc) 2 for 2 days (under Ar atmosphere)—4 days (under air). Pd(OAc) 2 was gradually absorbed by fibroin and the rapid reduction of fibroin conjugated Pd(OAc) 2 proceeded with MeOH as a reductant at room...

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Bibliographic Details
Published inTetrahedron Vol. 61; no. 8; pp. 2217 - 2231
Main Authors Ikawa, Takashi, Sajiki, Hironao, Hirota, Kosaku
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 21.02.2005
Elsevier
Subjects
Chemistry
Chemistry, Organic
Chemoselective
Hydrogenation
Palladium catalyst
Physical Sciences
Science & Technology
Silk-fibroin
Silk-fibroin
Palladium catalyst
Hydrogenation
Chemoselective
silk-fibroin
RETENTION
COMPLEXES
palladium catalyst
DEPROTECTION
hydrogenation
PD/C
ALCOHOLS
BENZYL
REDUCTION
CHLORIDES
chemoselective
N-CBZ
GENERAL PROCEDURE
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Summary:A palladium–fibroin complex (Pd/Fib) was prepared by soaking silk-fibroin in MeOH solution of Pd(OAc) 2 for 2 days (under Ar atmosphere)—4 days (under air). Pd(OAc) 2 was gradually absorbed by fibroin and the rapid reduction of fibroin conjugated Pd(OAc) 2 proceeded with MeOH as a reductant at room temperature to be the Pd(0) complex. Pd/Fib catalyzed chemoselective hydrogenation of acetylenes, olefins and azides in the presence of aromatic ketones and aldehydes, halides, N-Cbz protective groups and benzyl esters which are readily hydrogenated using Pd/C or Pd/C(en) as a catalyst. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2004.11.080