Pd/C-catalyzed reductive carbonylation of nitroaromatics for the synthesis of unsymmetrical ureas: one-step synthesis of neburon

被引:10
作者
Li, Chong-Liang [1 ]
Peng, Jin-Bao [1 ]
Qi, Xinxin [1 ]
Ying, Jun [1 ]
Wu, Xiao-Feng [1 ,2 ]
机构
[1] Zhejiang Sci Tech Univ, Dept Chem, Xiasha Campus, Hangzhou 310018, Zhejiang, Peoples R China
[2] Univ Rostock, Leibniz Inst Katalyse eV, Albert Einstein Str 29a, D-18059 Rostock, Germany
关键词
EMPLOYING FORMIC-ACID; SYMMETRICAL 1,3-DIARYLUREAS; CO SOURCE; ARYL HALIDES; NITROARENES; CONVENIENT; INHIBITORS; ISOCYANATES; DESIGN; AMINES;
D O I
10.1039/c8nj02413h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A Pd/C catalyzed reductive carbonylation of nitroarenes for the synthesis of unsymmetrical ureas has been developed. Using inexpensive and stable nitroarenes as the substrates, a series of unsymmetrical ureas were produced in moderate to good yields. A range of functional groups including thioethers, halides and vinyl were compatible with this reaction. As a heterogeneous catalyst, Pd/C was recycled and reused four times without Losing activity. Notably, urea-based herbicide neburon was prepared in 64% yield under our standard conditions.
引用
收藏
页码:12472 / 12475
页数:4
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共 61 条
[1]   CuI catalyzed C-S bond formation by using nitroarenes [J].
Bahekar, Sushilkumar S. ;
Sarkate, Aniket P. ;
Wadhai, Vijay M. ;
Wakte, Pravin S. ;
Shinde, Devanand B. .
CATALYSIS COMMUNICATIONS, 2013, 41 :123-125
[2]   Selected syntheses of ureas through phosgene substitutes [J].
Bigi, F ;
Maggi, R ;
Sartori, G .
GREEN CHEMISTRY, 2000, 2 (04) :140-148
[3]   A novel synthesis of isocyanates and ureas via β-elimination of haloform [J].
Braverman, S ;
Cherkinsky, M ;
Kedrova, L ;
Reiselman, A .
TETRAHEDRON LETTERS, 1999, 40 (16) :3235-3238
[4]   Fate of diuron and terbuthylazine in soils amended with two-phase olive oil mill waste [J].
Cabrera, A. ;
Cox, Lucia ;
Velarde, P. ;
Koskinen, William C. ;
Cornejo, Juan .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2007, 55 (12) :4828-4834
[5]   Pyrrolidine-ureas as bifunctional organocatalysts for asymmetric Michael addition of ketone to nitroalkenes: unexpected hydrogen bonding effect [J].
Cao, Xiao-Yu ;
Zheng, Jun-Cheng ;
Li, Yu-Xue ;
Shu, Zhen-Cao ;
Sun, Xiu-Li ;
Wang, Bi-Qin ;
Tang, Yong .
TETRAHEDRON, 2010, 66 (51) :9703-9707
[6]   Amide synthesis via nickel-catalysed reductive aminocarbonylation of aryl halides with nitroarenes [J].
Cheung, Chi Wai ;
Ploeger, Marten Leendert ;
Hu, Xile .
CHEMICAL SCIENCE, 2018, 9 (03) :655-659
[7]   Direct amidation of esters with nitroarenes [J].
Cheung, Chi Wai ;
Ploeger, Marten Leendert ;
Hu, Xile .
NATURE COMMUNICATIONS, 2017, 8
[8]   Synthesis and Properties of Polyurethane-Urea-Based Liquid Bandage Materials [J].
Choi, Soo-Jeong ;
Lee, Jung-Hee ;
Lee, Young-Hee ;
Hwang, Dae-Youn ;
Kim, Han-Do .
JOURNAL OF APPLIED POLYMER SCIENCE, 2011, 121 (06) :3516-3524
[9]   Synthesis of Methyl-1-(tert-butoxycarbonylamino)-2-vinylcyclopropanecarboxylate via a Hofmann Rearrangement Utilizing Trichloroisocyanuric Acid as an Oxidant [J].
Crane, Zackary D. ;
Nichols, Paul J. ;
Sammakia, Tarek ;
Stengel, Peter J. .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (01) :277-280
[10]   Small-molecule H-bond donors in asymmetric catalysis [J].
Doyle, Abigail G. ;
Jacobsen, Eric N. .
CHEMICAL REVIEWS, 2007, 107 (12) :5713-5743