Progress in the Study of Dehydroxymethylation of Primary Alcohol

  • Xinqiang Chen ,
  • Jing Zhang
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  • The Institute for Advanced Studies, Wuhan University, Wuhan 430000

Received date: 2023-03-04

  Revised date: 2023-04-04

  Online published: 2023-04-14

Supported by

The National Natural Science Foundation of China(22071185); The National Natural Science Foundation of China(22271224); The Fundamental Research Funds for the Central Universities(2042019kf0008); The Wuhan University Startup Funding

Abstract

Primary alcohols are abundant and readily available, which have been widely used as feedstock chemicals for the synthesis of agrochemicals, food additives, fragrances, pharmaceuticals and so on. The dehydroxymethylation reaction is an effective strategy to prepare hydrocarbons with one less carbon atom from primary alcohols, which has attracted tremendous attentions of many organic chemists and applied in biomass degradation and drug synthesis. The development of dehydroxy- methylation of primary alcohol on the base of the reaction characters is reviewed, including transition-metal catalyzed dehydroxymethylation to access methane and water, transition-metal catalyzed dehydroxymethylation to produce carbon monoxide and hydrogen, transition-metal catalyzed dehydroxymethylation to generate formaldehyde, as well as transition-metal free dehydroxymethylation to furnish formic acid and water. Each type of reaction is systematically summarized according to the catalytic system, the substrates scope and reaction mechanism.

Cite this article

Xinqiang Chen , Jing Zhang . Progress in the Study of Dehydroxymethylation of Primary Alcohol[J]. Chinese Journal of Organic Chemistry, 2023 , 43(8) : 2711 -2719 . DOI: 10.6023/cjoc202303009

References

[1]
Lutz, M. D. R.; Morandi, B. Chem. Rev. 2021, 121, 300.
[2]
Dong, X.-J.; Jin, W.-W.; Liu, C.-J. Chin. J. Org. Chem. 2020, 40, 1860. (in Chinese)
[2]
( 董晓娟, 金伟伟, 刘晨江, 有机化学, 2020, 40, 1860.)
[3]
Contente, M. L.; Paradisi, F. Nat. Catal. 2018, 1, 452.
[4]
Ahn, Y.; Ko, S.-B.; Kim, M.-J.; Park, J. Coord. Chem. Rev. 2008, 252, 647.
[5]
Modak, A.; Maiti, D. Org. Biomol. Chem. 2016, 14, 21.
[6]
Zeng, H.; Yu, J.; Li, C. J. Chem. Commun. 2020, 56, 1239.
[7]
Zhang, S.-X.; Li, X.-R.; Li, W.-X.; Rao, W.-D.; Ge, D.-H.; Shen, Z.-L.; Chu, X.-Q. Chin. J. Org. Chem. 2022, 42, 235. (in Chinese)
[7]
( 张斯旋, 李祥瑞, 李文欣, 饶卫东, 葛丹华, 沈志良, 褚雪强, 有机化学, 2022, 42, 235.)
[8]
Xue, X.; Weng, Y.; Yang, S.; Meng, S.; Sun, Q.; Zhang, Y. RSC Adv. 2021, 11, 6163.
[9]
Surisetty, V. R.; Dalai, A. K.; Kozinski, J. Appl. Catal., A 2011, 404, 1.
[10]
Norjannah, B.; Ong, H. C.; Masjuki, H. H.; Juan, J. C.; Chong, W. T. RSC Adv. 2016, 6, 60034.
[11]
Chen, B.-S.; Ribeiro de Souza, F. Z. RSC Adv. 2019, 9, 2102.
[12]
Tian, Z.-W.; Da, W.-M.; Wang, L.; Yang, Y.-S.; Wei, M. Acta Chim. Sinica 2022, 80, 1322. (in Chinese)
[12]
( 田钊炜, 达伟民, 王雷, 杨宇森, 卫敏, 化学学报, 2022, 80, 1322.)
[13]
Liu, H.; Dong, C.; Zhang, Z.; Wu, P.; Jiang, X. Angew. Chem., Int. Ed. 2012, 51, 12570.
[14]
Christensen, S. H.; Olsen, E. P.; Rosenbaum, J.; Madsen, R. Org. Biomol. Chem. 2015, 13, 938.
[15]
Kumar, A.; Shah, B. A. Org. Lett. 2015, 17, 5232.
[16]
Park, H.-S.; Kim, D.-S.; Jun, C.-H. ACS Catal. 2015, 5, 397.
[17]
Huang, G.; Lu, L.; Jiang, H.; Yin, B. Chem. Commun. 2017, 53, 12217.
[18]
Wu, X.; Cruz, F. A.; Lu, A.; Dong, V. M. J. Am. Chem. Soc. 2018, 140, 10126.
[19]
Hu, X.; Li, G.-X.; He, G.; Chen, G. Org. Chem. Front. 2019, 6, 3205.
[20]
Chen, Y.; Wang, X.; He, X.; An, Q.; Zuo, Z.-W J. Am. Chem. Soc. 2021, 143, 4896.
[21]
Gao, Y.; Liu, J.; Wei, C.; Li, Y.; Zhang, K.; Song, L.; Cai, L. Nat. Commun. 2022, 13, 7450.
[22]
Mahajan, B.; Aand, D.; Singh, A. K. ChemistrySelect 2018, 3, 12336.
[23]
Yu, X.; Wang, J.; Guo, W.; Tian, Y.; Wang, J. Organometallics 2016, 35, 1876.
[24]
Zhou, X.; Ding, H.; Chen, P.; Liu, L.; Sun, Q.; Wang, X.; Wang, P.; Lv, Z.; Li, M. Angew. Chem., Int. Ed. 2020, 59, 4138.
[25]
Liu, M.; Zhang, Z.; Liu, H.; Wu, T.; Han, B. Chem. Commun. 2020, 56, 7120.
[26]
Chheda, J. N.; Huber, G. W.; Dumesic, J. A. Angew. Chem., Int. Ed. 2007, 46, 7164.
[27]
Gallezot, P. ChemSusChem 2008, 1, 734.
[28]
Marshall, A. L.; Alaimo, P. J. Chem.-Eur. J. 2010, 16, 4970.
[29]
Zakzeski, J.; Bruijnincx, P. C.; Jongerius, A. A. L.; Weckhuysen, B. M. Chem. Rev. 2010, 110, 3552.
[30]
Serrano-Ruiz, J. C.; Dumesic, J. A. Energy Environ. Sci. 2011, 4, 83.
[31]
Li, H.; Wu, H.; Yu, Z.; Zhang, H.; Yang, S. ChemSusChem 2020, 13, 3565.
[32]
Agarwal, S.; Al-Abed, S. R.; Dionysiou, D. D. Environ. Sci. Technol. 2007, 41, 3722.
[33]
Monrad, R. N.; Madsen, R. J. Org. Chem. 2007, 72, 9782.
[34]
Agarwal, S.; Al-Abed, S. R.; Dionysiou, D. D. Environ. Sci. Technol. 2009, 43, 915.
[35]
Yamaguchi, S.; Kondo, H.; Uesugi, K.; Sakoda, K.; Jitsukawa, K.; Mitsudome, T.; Mizugaki, T. ChemCatChem 2021, 13, 1135.
[36]
Zhang, Z.; Zijlstra, D. S.; Lahive, C. W.; Deuss, P. J. Green Chem. 2020, 22, 3791.
[37]
Kreis, M.; Palmelund, A.; Bunch, L.; Madsen, R. Adv. Synth. Catal. 2006, 348, 2148.
[38]
Fessard, T. C.; Andrews, S. P.; Motoyoshi, H.; Carreira, E. M. Angew. Chem., Int. Ed. 2007, 46, 9331.
[39]
Iwai, T.; Fujihara, T.; Tsuji, Y. Chem. Commun. 2008, 6215.
[40]
Br?se, S.; Br?hmer, M.; Volz, N. Synlett 2009, 1383.
[41]
Akanksha; Maiti, D. Green Chem. 2012, 14, 2314.
[42]
Modak, A.; Deb, A.; Patra, T.; Rana, S.; Maity, S.; Maiti, D. Chem. Commun. 2012, 48, 46.
[43]
Roa, A. E.; Salazar, V.; López-Serrano, J.; O?ate, E.; Paneque, M.; Poveda, M. L. Organometallics 2012, 31, 716.
[44]
Huang, Y. B.; Yang, Z.; Chen, M. Y.; Dai, J. J.; Guo, Q. X.; Fu, Y. ChemSusChem 2013, 6, 1348.
[45]
Gutmann, B.; Elsner, P.; Glasnov, T.; Roberge, D. M.; Kappe, C. O. Angew. Chem., Int. Ed. 2014, 53, 11557.
[46]
Mitra, J.; Zhou, X.; Rauchfuss, T. Green Chem. 2015, 17, 307.
[47]
Shokri, A.; Que, L., Jr. J. Am. Chem. Soc. 2015, 137, 7686.
[48]
Hattori, T.; Takakura, R.; Ichikawa, T.; Sawama, Y.; Monguchi, Y.; Sajiki, H. J. Org. Chem. 2016, 81, 2737.
[49]
Ding, K.; Xu, S.; Alotaibi, R.; Paudel, K.; Reinheimer, E. W.; Weatherly, J. J. Org. Chem. 2017, 82, 4924.
[50]
Chatterjee, M.; Ishizaka, T.; Kawanami, H. Green Chem. 2018, 20, 2345.
[51]
Li, W. H.; Li, C. Y.; Li, Y.; Tang, H. T.; Wang, H. S.; Pan, Y. M.; Ding, Y. J. Chem. Commun. 2018, 54, 8446.
[52]
Matsuyama, T.; Yatabe, T.; Yabe, T.; Yamaguchi, K. ACS Catal. 2021, 11, 13745.
[53]
Lu, H.; Yu, T. Y.; Xu, P. F.; Wei, H. Chem. Rev. 2021, 121, 365.
[54]
B?eseken, J.; van Senden, G. H. Recl. Trav. Chim. Pays-Bas Belg. 1913, 32, 23.
[55]
Wojcik, B.; Adkins, H. J. Am. Chem. Soc. 1933, 55, 1293.
[56]
Adkins, H. Ind. Eng. Chem. Anal. Ed. 1932, 4, 342.
[57]
Covert, L. W.; Adkins, H. J. Am. Chem. Soc. 1932, 54, 4116.
[58]
Ipatieff, V. N.; Monroe, G. S.; Fischer, L. E.; Meisinger, E. E. Ind. Eng. Chem. 1949, 41, 1802.
[59]
Ipatieff, V. N.; Thompson, W. W.; Pines, H. J. Am. Chem. Soc. 1951, 73, 553.
[60]
Ipatieff, V. N.; Czajkowski, G. J.; Pines, H. J. Am. Chem. Soc. 1951, 73, 4098.
[61]
Pines, H.; Rodenberg, H. G.; Ipatieff, V. N. J. Am. Chem. Soc. 1953, 75, 6065.
[62]
Pines, H.; Rodenberg, H. G.; Ipatieff, V. N. J. Am. Chem. Soc. 1954, 76, 771.
[63]
Pines, H.; Shamaiengar, M.; Postl, W. S. J. Am. Chem. Soc. 1955, 77, 5099.
[64]
Reinecke, M. G.; Grins, G.; Kray, L. R.; Francis, R. F. Ann. N. Y. Acad. Sci. 1967, 145, 116.
[65]
Masayoshi, I.; Koji, S.; Masatoshi, K.; Kazuo, H. Bull. Chem. Soc. Jpn. 1970, 43, 2186.
[66]
Maier, W. F.; Grubmüller, P.; Thies, I.; Stein, P. M.; McKervey, M. A.; Schleyer, P. V. R. Angew. Chem., Int. Ed. Engl. 1979, 18, 939.
[67]
Di, L.; Yao, S.; Li, M.; Wu, G.; Dai, W.; Wang, G.; Li, L.; Guan, N. ACS Catal. 2015, 5, 7199.
[68]
Mizugaki, T.; Togo, K.; Maeno, Z.; Mitsudome, T.; Jitsukawa, K.; Kaneda, K. Sci. Rep. 2017, 7, 14007.
[69]
Kim, C.; Matsui, Y.; Orchin, M. J. Organomet. Chem. 1985, 279, 159.
[70]
Olsen, E. P.; Madsen, R. Chem.-Eur. J. 2012, 18, 16023.
[71]
Olsen, E. P.; Singh, T.; Harris, P.; Andersson, P. G.; Madsen, R. J. Am. Chem. Soc. 2015, 137, 834.
[72]
Ho, H. A.; Manna, K.; Sadow, A. D. Angew. Chem., Int. Ed. 2012, 51, 8607.
[73]
Modak, A.; Naveen, T.; Maiti, D. Chem. Commun. 2013, 49, 252.
[74]
Mazziotta, A.; Madsen, R. Eur. J. Org. Chem. 2017, 2017, 5417.
[75]
Pedersen, M. J.; Madsen, R.; Clausen, M. H. Chem. Commun. 2018, 54, 952.
[76]
Peng, L.; Ma, M.; Zhang, X.; Zhang, S.; Wang, J. Tetrahedron Lett. 2006, 47, 8175.
[77]
Zhang, K.; Chang, L.; An, Q.; Wang, X.; Zuo, Z.-W. J. Am. Chem. Soc. 2019, 141, 10556.
[78]
Xia, A.; Qi, X.; Mao, X.; Wu, X.; Yang, X.; Zhang, R.; Xiang, Z.; Lian, Z.; Chen, Y.; Yang, S. Org. Lett. 2019, 21, 3028.
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