Citation: ZHAO Qing-ning, SONG Qing-wen, LIU Ping, ZHANG Kan, HAO Jian. Ag(Ⅰ)/(ⁿC₇H₁₅)₄NBr-catalyzed reaction of ammonium carbamates and propargylic alcohols:Quantitative conversion of CO₂ into β-oxopropylcarbamates[J]. Journal of Fuel Chemistry and Technology, ;2018, 46(8): 1009-1017. shu

Ag(Ⅰ)/(ⁿC₇H₁₅)₄NBr-catalyzed reaction of ammonium carbamates and propargylic alcohols:Quantitative conversion of CO₂ into β-oxopropylcarbamates

ZHAO Qing-ning ¹ ,
SONG Qing-wen ^2,, ,
LIU Ping ² ,
ZHANG Kan ^2,, ,
HAO Jian ^1,3,,

1.
Department of Chemistry, Shanghai University, Shanghai 200444, China
2.
State Key Laboratory of Coal Conversion, Institute of Coal Chemistry, Chinese Academy of Sciences, Taiyuan 030001, China
3.
Basic Research Institute of Cultural Heritage Protection, Shanghai University, Shanghai 200444, China

Corresponding author: SONG Qing-wen, songqingwen@sxicc.ac.cn ZHANG Kan, zhangkan@sxicc.ac.cn HAO Jian, jhao@shu.edu.cn
Received Date: 25 April 2018
Revised Date: 20 June 2018

Fund Project: the National Natural Science Foundation of China 21672139the Natural Science Foundation of Shanxi Province 201701D221057the National Natural Science Foundation of China 21602232The project was supported by the National Natural Science Foundation of China (21602232, 21672139) and the Natural Science Foundation of Shanxi Province (201701D221057)

Figures(5)

A simple dual-component catalytic system, i.e., Ag(Ⅰ)/(ⁿC₇H₁₅)₄NBr was applied for the synthesis of various β-oxopropylcarbamates via dual-component coupling of ammonium carbamates and propargylic alcohols under atmospheric pressure.This simple method was proved to be a highly efficient system without the use of ligand, and capable of converting various propargylic alcohols and secondary amines into corresponding organic carbamates.Notably, quantitative conversion of CO₂ was achieved, thus improved the efficiency of CO₂ utilization.
- CO₂ conversion,
- ammonium carbamates,
- silver catalysis,
- β-oxopropylcarbamates,
- synthetic method
1. [1]
  HE Liang-nian.CO₂ Chemistry[M].Beijing:Science Press, 2013.
2. [2]
  SAKAKURA T, CHOI J C, YASUDA H. Transformation of carbon dioxide[J]. Chem Rev, 2007,107(6):2365-2387. doi: 10.1021/cr068357u
3. [3]
  SONG Q W, ZHOU Z H, HE L N. Efficient, selective and sustainable catalysis of carbon dioxide[J]. Green Chem, 2017,19(16):3707-3728. doi: 10.1039/C7GC00199A
4. [4]
  GAO Jian, MIAO Cheng-xia, WANG Jing-lun, HE Liang-nian. Recent advances in utilization of carbon dioxide as a renewable resource[J]. Petrochem Technol, 2010,39(5):465-475.
5. [5]
  HE M Y, SUN Y H, HAN B X. Green carbon science:Scientific basis for integrating carbon resource processing, utilization, and recycling[J]. Angew Chem Int Ed, 2013,52(37):9620-9633. doi: 10.1002/anie.201209384
6. [6]
  LIU An-hua, HE Liang-nian, GAO Jian, YANG Zhen-zhen, LI Yu-nong, LI Bin, YU Bing. Carbon dioxide chemistry:Catalytic conversion of CO₂ into value-added fuels and chemicals[J]. Chin J Synth Chem, 2010,18(S1):80-91.
7. [7]
  ARESTA M, DIBENEDETTO A, FRACCHIOLLA E, GIANNOCCARO P, PASTORE C, PÁPAI I, SCHUBERT G. Mechanism of formation of organic carbonates from aliphatic alcohols and carbon dioxide under mild conditions promoted by carbodiimides.DFT calculation and experimental study[J]. J Org Chem, 2005,70(16):6177-6186. doi: 10.1021/jo050392y
8. [8]
  YAMAZAKI Y, KAKUMA K, DU Y, SAITO S. Synthesis of carbonates directly from 1 atm CO₂ and alcohols using CH₂Cl₂[J]. Tetrahedron, 2010,66(51):9675-9680. doi: 10.1016/j.tet.2010.10.051
9. [9]
  KINDERMANN N, JOSE T, KLEIJ A W. Synthesis of carbonates from alcohols and CO₂[J]. Top Curr Chem, 2017,375(1)15. doi: 10.1007/s41061-016-0101-8
10. [10]
  SHI F, DENG Y, SIMA T L, PENG J J, GU Y L, QIAO B T. Alternatives to phosgene and carbon monoxide:Synthesis of symmetric urea derivatives with carbon dioxide in ionic liquids[J]. Angew Chem Int Ed, 2003,42(28):3257-3260. doi: 10.1002/anie.200351098
11. [11]
  JIANG T, MA X, ZHOU Y X, LIANG S G, ZHANG J, HAN B X. Solvent-free synthesis of substituted ureas from CO₂ and amines with a functional ionic liquid as the catalyst[J]. Green Chem, 2008,10(4):465-469. doi: 10.1039/b717868a
12. [12]
  WU C, CHENG H, LIU R X, WANG Q, HAO Y F, YU Y C, ZHAO F Y. Synthesis of urea derivatives from amines and CO₂ in the absence of catalyst and solvent[J]. Green Chem, 2010,12(10):1811-1816. doi: 10.1039/c0gc00059k
13. [13]
  STIEBER S C E, HUGUET N, KAGEYAMA T, JEVTOVIKJ I, ARIYANANDA P, GORDILLO A, SCHUNK S A, ROMINGER F, HOFMANN P, LIMBACH M. Acrylate formation from CO₂ and ethylene:Catalysis with palladium and mechanistic insight[J]. Chem Commun, 2015,51(54):10907-10909. doi: 10.1039/C5CC01932J
14. [14]
  KNOPF I, TOFAN D, BEETSTRA D, NEZARI A A, BAHILY K A, CUMMINS C C. A family of cis-macrocyclic diphosphines:Modular, stereoselective synthesis and application in catalytic CO₂/ethylene coupling[J]. Chem Sci, 2017,8(2):1463-1468. doi: 10.1039/C6SC03614G
15. [15]
  YU D, ZHANG Y. Copper-and copper-N-heterocyclic carbene-catalyzed C-H activating carboxylation of terminal alkynes with CO₂ at ambient conditions[J]. Proc Natl Acad Sci, 2010,107(47):20184-20189. doi: 10.1073/pnas.1010962107
16. [16]
  KIM S H, KIM K H, HONG S H. Carbon dioxide capture and use:organic synthesis using carbon dioxide from exhaust gas[J]. Angew Chem Int Ed, 2014,53(3):771-774. doi: 10.1002/anie.201308341
17. [17]
  JI Dong-feng, WANG Hui, HE Ren. Study on chemical fixation of CO₂ and syntheses of alkylene carbonate[J]. J Fuel Chem Technol, 2001,29(6):486-489.
18. [18]
  YOSHIDA S, FUKUI K, KIKUCHI S, YAMADA T. Silver-catalyzed enantioselective carbon dioxide incorporation into bispropargylic alcohols[J]. J Am Chem Soc, 2010,132(12):4072-4073. doi: 10.1021/ja1007118
19. [19]
  TAMURA M, HONDA M, NORO K, NAKAGAWA Y, TOMISHIGE K. Heterogeneous CeO₂-catalyzed selective synthesis of cyclic carbamates from CO₂ and aminoalcohols in acetonitrile solvent[J]. J Catal, 2013,305:191-203. doi: 10.1016/j.jcat.2013.05.013
20. [20]
  HU J, MA J, ZHU Q L, QIAN Q L, HAN H L, MEI Q Q, HAN B X. Zinc (Ⅱ)-catalyzed reactions of carbon dioxide and propargylic alcohols to carbonates at room temperature[J]. Green Chem, 2016,18(2):382-385. doi: 10.1039/C5GC01870F
21. [21]
  YANG Z Z, HE L N, ZHAO Y N, LI B, YU B. CO₂ capture and activation by superbase/polyethylene glycol and its subsequent conversion[J]. Energy Environ Sci, 2011,4(10):3971-3975. doi: 10.1039/c1ee02156g
22. [22]
  LIU A H, MA R, SONG C, YANG Z Z, YU A, CAI Y, HE L N, ZHAO Y N, YU B, SONG Q W. Equimolar CO₂ capture by N-substituted amino acid salts and subsequent conversion[J]. Angew Chem Int Ed, 2012,51(45):11306-11310. doi: 10.1002/anie.201205362
23. [23]
  BARZAGLI F, LAI S, MANI F. A new class of single-component absorbents for reversible carbon dioxide capture under mild conditions[J]. ChemSusChem, 2015,8(1):184-191. doi: 10.1002/cssc.201402421
24. [24]
  SONG Q W, ZHOU Z H, YIN H, HE L N. Silver(Ⅰ)-catalyzed synthesis of β-oxopropylcarbamates from propargylic alcohols and CO₂ surrogate:A gas-free process[J]. ChemSusChem, 2015,8(23):3967-3972. doi: 10.1002/cssc.201501176
25. [25]
  YU B, CHENG B B, LIU W Q, LI W, WANG S S, CAO J, HU C W. Atmospheric pressure of CO₂ as protecting reagent and reactant:Efficient synthesis of oxazolidin-2-ones with carbamate salts, aldehydes and alkynes[J]. Adv Synth Catal, 2016,358(1):90-97. doi: 10.1002/adsc.v358.1
26. [26]
  REZAYEE N M, HUFF C A, SANFORD M S. Tandem amine and ruthenium-catalyzed hydrogenation of CO₂ to methanol[J]. J Am Chem Soc, 2015,137(3):1028-1031. doi: 10.1021/ja511329m
27. [27]
  SASAKI Y, DIXNEUF P H. Ruthenium-catalyzed reaction of carbon dioxide, amine, and acetylenic alcohol[J]. J Org Chem, 1987,52(19):4389-4391. doi: 10.1021/jo00228a046
28. [28]
  BRUNEAU C, DIXNEUF P H. Catalytic synthesis of O-β-oxoalkylcarbamates[J]. Tetrahedron Lett, 1987,28(18):2005-2008. doi: 10.1016/S0040-4039(00)96031-3
29. [29]
  KIM T J, KWON K H, KWON S C, BAEG J O, SHIM S C. Iron complexes of 1, 1'-bis (diphenylphosphino)ferrocene(BPPF) as efficient catalysts in the synthesis of carbamates.X-ray crystal structure of (BPPF)Fe(CO)₃[J]. J Organomet Chem, 1990,389(2):205-217. doi: 10.1016/0022-328X(90)85412-R
30. [30]
  KIM H S, KIM J W, KWON S C, SHIM S C, KIM T J. Catalytic formation of carbamates and cyclic carbonates by copper complex of 2, 5, 19, 22-tetraaza[6, 6] (1, 1')ferrocenophane-1, 5-diene X-ray crystal structure of[Cu(1)]PF₆[J]. J Organomet Chem, 1997,545:337-344.
31. [31]
  LI Xue-dong, LANG Xian-dong, SONG Qing-wen, GUO Ya-kun, HE Liang-nian. Cu(Ⅰ)-catalyzed three-component reaction of propargylic alcohol, secondary amines and atmospheric CO₂[J]. Chin J Org Chem, 2016,36:744-751.
32. [32]
  QI C, HUANG L, JIANG H. Efficient synthesis of β-oxoalkyl carbamates from carbon dioxide, internal propargylic alcohols, and secondary amines catalyzed by silver salts and DBU[J]. Synthesis, 2010,41(35):1433-1440.
33. [33]
  SONG Q W, YU B, LI X D, MA R, DIAO Z F, LI R G, LI W, HE L N. Efficient chemical fixation of CO₂ promoted by a bifunctional Ag₂WO₄/Ph₃P system[J]. Green Chem, 2014,16(3):1633-1638. doi: 10.1039/c3gc42406e
34. [34]
  SONG Q W, CHEN W Q, MA R, YU A, LI Q Y, CHANG Y, HE L N. Bifunctional silver(Ⅰ) complex-catalyzed CO₂ conversion at ambient conditions:Synthesis of α-methylene cyclic carbonates and derivatives[J]. ChemSusChem, 2015,8(5):821-827. doi: 10.1002/cssc.v8.5
35. [35]
  SEKINE K, YAMADA T. Silver-catalyzed carboxylation[J]. Chem Soc Rev, 2016,45(16):4524-4532. doi: 10.1039/C5CS00895F
36. [36]
  SONG Q W, LIU P, HAN L H, ZHANG K, HE L N. Upgrading CO₂ by incorporation into urethanes through silver-catalyzed one-pot stepwise amidation reaction[J]. Chin J Chem, 2018,36(2):147-152. doi: 10.1002/cjoc.201700572
37. [37]
  CA N D, GABRIELE B, RUFFOLO G, VELTRI L, ZANETTA T, COSTA M. Effective guanidine-catalyzed synthesis of carbonate and carbamate derivatives from propargyl alcohols in supercritical carbon dioxide[J]. Adv Synth Catal, 2011,353(1):133-146. doi: 10.1002/adsc.201000607
38. [38]
  SONG Q W, HE L N. Robust silver(Ⅰ) catalyst for the carboxylative cyclization of propargylic alcohols with carbon dioxide under ambient conditions[J]. Adv Synth Catal, 2016,358(8):1251-1258. doi: 10.1002/adsc.v358.8
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Ag(Ⅰ)/(nC7H15)4NBr-catalyzed reaction of ammonium carbamates and propargylic alcohols:Quantitative conversion of CO2 into β-oxopropylcarbamates

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通讯作者: 陈斌, bchen63@163.com

Ag(Ⅰ)/(ⁿC₇H₁₅)₄NBr-catalyzed reaction of ammonium carbamates and propargylic alcohols:Quantitative conversion of CO₂ into β-oxopropylcarbamates