Safe Removal of the Allyl Protecting Groups of Allyl Esters using a Recyclable, Low-Leaching and Ligand-Free Palladium Nanoparticle Catalyst

被引：21

作者：

Takagi, Koji ^{[1
]}

Fukuda, Hayato ^{[1
]}

Shuto, Satoshi ^{[1
,4
]}

Otaka, Akira ^{[2
,3
]}

Arisawa, Mitsuhiro ^{[1
,5
]}

机构：

[1] Hokkaido Univ, Fac Pharmaceut Sci, Kita Ku, Sapporo, Hokkaido 0600812, Japan

[2] Univ Tokushima, Inst Biomed Sci, Tokushima 7708505, Japan

[3] Univ Tokushima, Grad Sch Pharmaceut Sci, Tokushima 7708505, Japan

[4] Hokkaido Univ, Ctr Res & Educ Drug Discovery, Kita Ku, Sapporo, Hokkaido 0600812, Japan

[5] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650862, Japan

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2015年 / 357卷 / 09期

关键词：

allyl ester; allyl protecting group; cleavage; deprotection; ester; nanoparticle; palladium; GOLD-SUPPORTED PALLADIUM; SIDE-CHAIN; DEPROTECTION; GLYCOPEPTIDES; CARBAPENEMS; DERIVATIVES; ENVIRONMENT; AMINATION; FACILE; ETHERS;

D O I：

10.1002/adsc.201500055

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A safe, facile and low-leaching (up to 0.04 ppm) method has been developed for the removal of allyl, prenyl and benzyl protecting groups from the corresponding esters, using a sulfur-modified gold-supported palladium (SAPd) nanoparticle catalyst, which is known to be non-flammable. The catalyst itself was found to be recyclable and the reaction appeared to proceed on the surface of the SAPd.

引用

页码：2119 / 2124

页数：6

共 5 条

[1] Ligand-Free Buchwald-Hartwig Aromatic Aminations of Aryl Halides Catalyzed by Low-Leaching and Highly Recyclable Sulfur-Modified Gold-Supported Palladium Material
Al-Amin, Mohammad
Honma, Tetsuo
Hoshiya, Naoyuki
Shuto, Satoshi
Arisawa, Mitsuhiro
ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (06) : 1061 - 1068
[2] Ligand-free palladium-catalysed direct arylation of heteroaromatics using low catalyst loadings
Pozgan, Franc
Roger, Julien
Doucet, Henri
CHEMSUSCHEM, 2008, 1 (05) : 404 - 407
[3] Facile removal strategy for allyl and allyloxycarbonyl protecting groups using solid-supported barbituric acid under palladium catalysis
Tsukamoto, H
Suzuki, T
Kondo, Y
SYNLETT, 2003, (08) : 1105 - 1108
[4] Chemoselective and ligand-free aerobic oxidation of benzylic alcohols to carbonyl compounds using alumina-supported mesoporous nickel nanoparticle as an efficient recyclable heterogeneous catalyst
Das, Asit Kumar
Nandy, Sneha
Bhar, Sanjay
APPLIED ORGANOMETALLIC CHEMISTRY, 2021, 35 (08)
[5] Ligand-free Suzuki-Miyaura coupling reaction of an aryl chloride using a continuous irradiation type microwave and a palladium nanoparticle catalyst: effect of a co-existing solid
Yamada, Makito
Shio, Yasunori
Akiyama, Toshiki
Honma, Tetsuo
Ohki, Yuuta
Takahashi, Naoyuki
Murai, Kenichi
Arisawa, Mitsuhiro
GREEN CHEMISTRY, 2019, 21 (16) : 4541 - 4549

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