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钯催化芳基偶氮的氧化羰基化反应(英文) 被引量:3

Palladium-Catalyzed Oxidative Carbonylation of Arylazos via N=N Double Bond Cleavage
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摘要 采用TBHP作为氧化剂,发展了钯催化芳基偶氮化合物N=N双键断裂的氧化羰基化反应.芳基偶氮的羰基化反应在Pd(OAc)2(5%),MeO-BIPHEP(5%),芳基偶氮(0.2 mmol),TBHP(2 equiv),H2O(1 equiv),DCE(1 mL),CO(3.0 MPa)的条件下110℃反应12 h后,经柱层析纯化分离得到31%-91%的芳基脲.初步的机理研究表明,芳基偶氮化合物的N=N双键断裂原位产生芳基胺,再进一步氧化羰基化生成芳基脲. A new palladium-catalyzed oxidative carbonylation of arylazos has been developed via cleavage of NN double bond with TBHP as oxidant,which provided an alternative method for synthesis of arylureas from simple arylazos. The desired products could be obtained in good to excellent yields( 31% ~ 90%) catalyzed by the combination of Pd( OAc)_2/ MeO-B IPHEP in the presence of TBHP at 110 ℃ under 3. 0 MPa of CO. The primary mechanistic studies demonstrated that amines might be first formed in situ from arylazos and then the oxidative carbonylation of amines occurs to give the urea products.
出处 《分子催化》 EI CAS CSCD 北大核心 2016年第3期207-213,共7页 Journal of Molecular Catalysis(China)
基金 supported by the Chinese Academy of Sciences and the National Natural Science Foundation of China(21172226 and21133011)
关键词 芳基偶氮 氧化羰基化 N=N键断裂 芳基脲 arylazos oxidative carbonylation N=N cleavage arylureas
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  • 1Yang L, Huang H M. Transition-metal-catalyzed direct addition of unactivated C-H bonds to polar unsaturated bonds [J]. Chem Rev, 2015, 115(9): 3468-3517.
  • 2OuyangK, Hao W, Xi Z F, et al. Transition-metal- catalyzed cleavage of C-N single bonds [ J ]. Chem Rev,2015, 115(21): 12045-12090.
  • 3张欣,杨彩玲,宋伟伟,张远丽,刘建明,卓克垒.离子液体制备纳米钯催化碘代芳烃双羰化反应合成α-酮酰胺[J].分子催化,2014,28(4):312-316. 被引量:13
  • 4马宇春,刘仲能,王德举,任杰,赵多.改性丝光沸石催化二甲醚气相羰化的反应性能[J].分子催化,2014,28(5):460-465. 被引量:3
  • 5Wang Q J, Su Y J, Huang H M, et al. Transition-me- tal catalysed C-N bond activation [ J ]. Chem Soc Rev, 2016, 45: 1257-1272.
  • 6刘蕊,熊绪茂,慕新元,马占伟,宋承立,胡斌.羰基铁催化乙炔羰化合成丙烯酸甲酯的研究[J].分子催化,2015,29(2):97-102. 被引量:5
  • 7Guan B T, Xiang S K, Shi Z J. et al. Direct benzylic al- kylation via Ni-catalyzed selective benzylic sp3 C-O acti- vation [ J ]. J Am Chem Soc, 2008, 130 ( 11 ) : 3268- 3269.
  • 8Murahashi S, Horiie S. The reaction of azobenzene and carbon monoxide [J]. J Am Chem Soc, 1956, 78(18) : 4816-4817.
  • 9Muniz K, Nieger M. Catalytic Activation of N--N Multi- ple Bonds: A homogeneous palladium catalyst for mecha- nistically unprecedented reduction of azo compounds [ J ]. Angew Chem lnt Ed, 2006, 45(14) : 2305-2308.
  • 10Bonyhady S J, Green S P, Stasch A, et al. A dimeric magnesium(I) compound as a facile two-center/two elec- tron reductant [J]. Angew Chem Int. Ed, 2009, 48(16) : 2973.

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