Sulfated tungstate: A highly efficient, recyclable and ecofriendly catalyst for chemoselective N-tert butyloxycarbonylation of amines under the solvent-free conditions

被引：4

作者：

Ingale, Ajit P. ^{[1
]}

Shinde, Sandeep, V ^{[2
]}

Thorat, Nitin M. ^{[3
]}

机构：

[1] Savitribai Phule Pune Univ, Dada Patil Coll, Dept Chem, Ahmednagar, Maharashtra, India

[2] Swami Ramanand Teerth Marathwada Univ, Pratibha Niketan Coll, Dept Chem, Nanded, India

[3] Savitribai Phule Pune Univ, Maharaja Jivajirao Shinde Coll, Dept Chem, Ahmednagar, India

来源：

SYNTHETIC COMMUNICATIONS | 2021年 / 51卷 / 16期

关键词：

Chemoselective; eco-friendly; N-tert-butyloxycarbonylation; solvent-free; sulfated tungstate; BOC PROTECTION; IONIC LIQUID; ORGANIC-SYNTHESIS; GREEN CHEMISTRY; ACID CATALYST; BUTOXYCARBONYLATION; MILD; TRANSAMIDATION; ORGANOCATALYST; TECHNOLOGY;

D O I：

10.1080/00397911.2021.1942060

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Sulfated tungstate catalyzed an efficient and ecofriendly protocol has been described for the chemoselective N-tert-butyloxycarbonylation of amines under the solvent-free conditions at room temperature. The variety of functionalized aliphatic, aromatic and heteroaromatic amines efficiently undergoes the N-tert-butyloxycarbonylation under the developed protocol. The aminoalcohol, aminophenol, aminoester as well as various chiral amines underwent the chemoselective N-Boc protection under the optimized reaction condition. The rapid reaction rate, mild conditions, very good functional group tolerance, excellent yield, solvent-free, easy recovery products and excellent catalyst recyclability are the advantages of this protocol. This makes the protocol feasible, economical and environmentally benign.

引用

页码：2528 / 2543

页数：16

共 99 条

[91] Efficient N-Boc protection of amines by a reusable heterogeneous solid acid nanocatalyst at room temperature [J].

Veisi, Hojat ;

Sedrpoushan, Alireza ;

Ghazizadeh, Habibollah ;

Hemmati, Saba .

RESEARCH ON CHEMICAL INTERMEDIATES, 2016, 42 (02) :1451-1461

[92] A rate enhancement of tert-butoxycarbonylation of aromatic amines with Boc2O in alcoholic solvents [J].

Vilaivan, Tirayut .

TETRAHEDRON LETTERS, 2006, 47 (38) :6739-6742

[93] Sulfated-Tungstate-Catalyzed Synthesis of Ureas/Thioureas via Transamidation and Synthesis of Forchlorofenuron [J].

Wagh, Ganesh D. ;

Pathare, Sagar P. ;

Akamanchi, Krishnacharya G. .

CHEMISTRYSELECT, 2018, 3 (25) :7049-7053

[94] Sulfated tungstate catalyzed synthesis of C3-symmetric 1,3,5-triaryl benzenes under solvent-free condition [J].

Wagh, Ganesh D. ;

Akamanchi, Krishnacharya G. .

TETRAHEDRON LETTERS, 2017, 58 (31) :3032-3036

[95]

Wuts P. G. M., 2007, GREENES PROTECTIVE G

[96] SIMPLE AND EFFICIENT METHOD FOR N-BOC PROTECTION OF AMINES USING PEG-400 AS A REACTION MEDIUM UNDER MILD CONDITIONS [J].

Zeng, Hongyao ;

Li, Yongjia ;

Shao, Huawu .

SYNTHETIC COMMUNICATIONS, 2012, 42 (01) :25-32

[97] Green chemistry aspects of fluorous techniques-opportunities and challenges for small-scale organic synthesis [J].

Zhang, Wei .

GREEN CHEMISTRY, 2009, 11 (07) :911-920

[98] Novel ionic liquid 1,3-disulfonic acid imidazolium hydrogen sulfate {[Dsim]HSO4} efficiently catalyzed N-boc protection of amines [J].

Zolfigol, M. A. ;

Khakyzadeh, V. ;

Moosavi-Zare, A. R. ;

Chehardoli, G. ;

Derakhshan-Panah, F. ;

Zare, A. ;

Khaledian, O. .

SCIENTIA IRANICA, 2012, 19 (06) :1584-1590

[99] Nano-ferrous ferric oxide (nano-Fe3O4): Powerful, reusable, and stable catalyst for N-Boc protection of amines [J].

Zolfigol, Mohammad Ali ;

Moosavi-Zare, Ahmad Reza ;

Moosavi, Parvin ;

Khakyzadeh, Vahid ;

Zare, Abdolkarim .

COMPTES RENDUS CHIMIE, 2013, 16 (11) :962-966

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