Hydrosilane-Promoted Facile Deprotection of tert-Butyl Groups in Esters, Ethers, Carbonates, and Carbamates

被引：4

作者：

Ikeda, Takuya ^{[1
]}

Zhang, Zhenzhong ^{[1
]}

Motoyama, Yukihiro ^{[1
]}

机构：

[1] Toyota Technol Inst, Dept Adv Sci & Technol, Nagoya, Aichi 4688511, Japan

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2019年 / 361卷 / 04期

关键词：

activated carbon; deprotection; hydrosilane; palladium; tert-butyl group; SILANE-REDUCTION; HECK REACTIONS; PALLADIUM; CLEAVAGE; CLUSTER; POLYMERIZATION; ALDEHYDES; REMOVAL;

D O I：

10.1002/adsc.201801279

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Combination of PdCl2 with 1,1,3,3-tetramethyldisiloxane in the presence of activated carbon was found to be an effective catalyst system for the cleavage reaction of C-O bond of O-t-Bu moieties. The present catalytic reaction offers a practical method for the deprotection of tert-butyl esters, tert-butyl ethers, O-Boc, and N-Boc derivatives under mild conditions. The addition of activated carbon in the reaction mixture was proved to be crucial for not only sustaining the catalytic activity but also trapping the palladium species after the reaction.

引用

页码：673 / 677

页数：5

共 46 条

[1] Triarylamminium Radical Cation Facilitates the Deprotection of tert-Butyl Groups in Esters, Ethers, Carbonates, and Carbamates
Hidasova, Denisa
Slanina, Tomas
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (11): : 6932 - 6938
[2] Florisil as an efficient reagent for deprotection of tert-butyl carbamates, carbonates and esters
Liu, Cheng-Hang
Xu, Mengyang
Luo, Qiyun
Wang, Ziyan
Tan, Wenyue
Zhao, Xingzeng
Jia, Xiaodong
TETRAHEDRON, 2024, 155
[3] Aqueous phosphoric acid as a mild reagent for deprotection of tert-butyl carbamates, esters, and ethers
Li, Bryan
Berliner, Martin
Buzon, Richard
Chiu, Charles K. -F.
Colgan, Stephen T.
Kaneko, Takushi
Keene, Nandell
Kissel, William
Le, Tung
Leeman, Kyle R.
Marquez, Brian
Morris, Ronald
Newell, Lisa
Wunderwald, Silke
Witt, Michael
Weaver, John
Zhang, Zhijun
Zhang, Zhongli
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (24): : 9045 - 9050
[4] Hydrosilanes Are Not Always Reducing Agents for Carbonyl Compounds, II: Ruthenium-Catalyzed Deprotection of tert-Butyl Groups in Carbamates, Carbonates, Esters, and Ethers
Hanada, Shiori
Yuasa, Akihiro
Kuroiwa, Hirotaka
Motoyama, Yukihiro
Nagashima, Hideo
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (06) : 1021 - 1025
[5] ORGN 470-Aqueous phosphoric acid as a mild reagent for deprotection of tert-butyl carbamates, esters and ethers
Li, Bryan
Berliner, Martin A.
Buzon, Richard A.
Chiu, Charles K-F
Colgan, Steve
Kaneko, Takushi
Keene, Nandell
Kissel, William S.
Le, Tung V.
Leeman, Kyle R.
Newell, Lisa
Weaver, John
Witt, Michael
Zhang, Zhijun
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 232
[6] A mild deprotection procedure for tert-butyl esters and tert-butyl ethers using ZnBr2 in methylene chloride
Wu, YQ
Limburg, DC
Wilkinson, DE
Vaal, MJ
Hamilton, GS
TETRAHEDRON LETTERS, 2000, 41 (16) : 2847 - 2849
[7] Deprotection of N-tert-butoxycarbonyl (Boc) groups in the presence of tert-butyl esters
Lin, LS
Lanza, T
de Laszlo, SE
Truong, Q
Kamenecka, T
Hagmann, WK
TETRAHEDRON LETTERS, 2000, 41 (36) : 7013 - 7016
[8] Facile deprotection of aromatic tert-butyl and allylic esters under microwave irradiation conditions
Lee, JC
Yoo, ES
Lee, JS
SYNTHETIC COMMUNICATIONS, 2004, 34 (16) : 3017 - 3020
[9] Mild deprotection of PMB ethers using tert-butyl bromide
Rival, Nicolas
Grados, Arantxa Albornoz
Schiavo, Lucie
Colobert, Francoise
Hanquet, Gilles
TETRAHEDRON LETTERS, 2015, 56 (49) : 6823 - 6826
[10] Selective deprotection of Boc in the presence of tert-butyl esters.
Hruby, V
Tamaki, M
Han, G
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 : U115 - U115

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