无碱条件下铜催化的苄醇在水中的氧化反应（英文）
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摘要
提出了一种由苄醇氧化为芳醛的方法,该方法反应条件温和、绿色环保,而且转换率高.该反应以双(8-羟基喹啉)铜(II)为催化剂,四甲基哌啶氮氧化物(TEMPO)为助催化剂,室温条件下直接在空气反应.这以方法提供了一种实用的合成芳醛的途径,具有环境友好、操作简单、收率高的优势.
A green and very mild method for the oxidation of benzyl alcohols to aromatic aldehydes with excellent conversions has been developed. The reaction could be carried out directly in air at room temperature and was catalyzed by bis(8-quinolinolato) copper(II) with 2,2,6,6-tetramethylpiperidine-1-oxyl(TEMPO) as co-catalysts. The methodology provided a practical approach for the synthesis of aromatic aldehydes, which has the advantages of environment-friendly, simple workup and high yields.
A green and very mild method for the oxidation of benzyl alcohols to aromatic aldehydes with excellent conversions has been developed. The reaction could be carried out directly in air at room temperature and was catalyzed by bis(8-quinolinolato) copper(II) with 2,2,6,6-tetramethylpiperidine-1-oxyl(TEMPO) as co-catalysts. The methodology provided a practical approach for the synthesis of aromatic aldehydes, which has the advantages of environment-friendly, simple workup and high yields.
引文
[1]Liu, W. X.; Wu, Y. Q.; Li, L. Z.; Li, X. Chin. J. Org. Chem. 2016,36, 1501(in Chinese).(刘文香,吴宇强,李灵芝,李霞,有机化学, 2016, 36, 1501.)
[2]Luo, F. H.; Long, Y.; Li, Z. K.; Zhou, X. G. Acta Chim. Sinica 2016,74, 805(in Chinese).(罗飞华,龙洋,李正凯,周向葛,化学学报, 2016, 74, 805.)
[3]Chen,Y.;Hu,A.H.;Yang,L.Y.;Li,Z.Y.;Yan,K.Chin.J.Org.Chem. 2017, 37, 1939(in Chinese).(陈燚,胡奥晗,杨凌毅,李早英,严琨,有机化学,2017,37,1939.)
[4]Bowden, K.; Heilbron, I. M.; Jones, E. R. H.; Weedon, B. C. L. J.Chem. Soc. 1946, 39.
[5]Corey, E. J.; Suggs, J. W. Tetrahedron Lett. 1975, 16, 2647.
[6]Piancatelli, G.; Scettri, A.; Auria, M. Synthesis 1982, 245.
[7]De, A. J. Sci. Ind. Res. 1982, 41, 484.
[8]Luzzio, F. A.; Guziec, F. S. Org. Prep. Proced. Int. 1988, 20, 533.
[9]Ladbury, J. W.; Cullis, C. F. Chem. Rev. 1958, 58, 403.
[10]Fatiadi, A. J. Synthesis 1976, 65.
[11]Taylor,R.J.K.;Reid,M.;Foot,J.;Raw,S.A.Acc.Chem.Res.2005, 38, 851.
[12]Semmelhack,M.F.;Schmid,C.R.;Cortes,D.A.;Chou,C.S.J.Am. Chem. Soc. 1984, 106, 3374.
[13]Gamez,P.;Arends,I.W.C.E.;Sheldon,R.A.;Reedijk,J.Adv.Synth. Catal. 2004, 346, 805.
[14]Jiang, N.; Ragauskas, A. J. J. Org. Chem. 2006, 71, 7087.
[15]Figiel,P.J.;Sibaouih,A.;Ahmad,J.U.;Nieger,M.;Leskela,M.;Repo, T. Adv. Synth. Catal. 2009, 351, 2625.
[16]Konning, D.; Hiller, W.; Christmann, M. Org. Lett. 2012, 14, 5258.
[17]Hoover, J. M.; Steves, J. E.; Stahl, S. S. Nat. Protoc. 2012, 7, 1161.
[18]Ragagnin,G.;Betzemeier,B.;Quici,S.;Knochel,P.Tetrahedron2002, 58, 3985.
[19]Betzemeier,B.Cavazzini,M.;Quici,S.;Knochel,P.Tetrahedron Lett. 2000, 41, 4343.
[20]Ansari, I. A.; Gree, R. Org. Lett. 2002, 4, 1507.
[21]Liu, K. J.; Fu,Y. L.; Xie, L. Y.; Wu, C.; He, W. B.; Peng, S.; Wang,Z.;Bao,W.H.;Cao,Z.;Xu,X.H.;He,W.M.ACSSustainable Chem. Eng. 2018, 6, 4916.
[22]Jiang, X. G.; Zhai, Y. Z.; Chen, J. Y.; Han,Y. L.; Yang, Z.; Ma, S. M.Chin. J. Chem. 2018, 36, 15.
[23]Steves, J. E.; Stahl, S. S. J. Am. Chem. Soc. 2013, 135, 15742.
[24]Gamez, P.; Reedijk, J.; Sheldon, R. A. Chem. Commun. 2003, 2414.
[25]Hoover, J. M.; Stahl, S. S. J. Am. Chem. Soc. 2011, 133, 16901.
[26]Kumpulainen, E. T. T.; Koskinen, A. M. P. Chem.-Eur. J. 2009, 15,10901.
[27]Steves, J. E.; Stahl, S. S. J. Org. Chem. 2015, 80, 11184.
[28]Hill, N. J.; Hoover, J. M.; Stahl, S. S. J. Chem. Educ. 2013, 90, 102.
[29]Hoover, J. M.; Ryland, B. L.; Stahl, S. S. ACS Catal. 2013, 3, 2599.
[30]Corre, Y.; Rysak, V.; Capet, F.; Djukic, J. P.; Agbossou-Niedercorn,F.; Michon, C. Chemistry 2016, 22, 14036.
[31]Zhan, L. W.; Han, L.; Xing, P.; Jiang, B. Chemistry 2016, 47, 5990.
[2]Luo, F. H.; Long, Y.; Li, Z. K.; Zhou, X. G. Acta Chim. Sinica 2016,74, 805(in Chinese).(罗飞华,龙洋,李正凯,周向葛,化学学报, 2016, 74, 805.)
[3]Chen,Y.;Hu,A.H.;Yang,L.Y.;Li,Z.Y.;Yan,K.Chin.J.Org.Chem. 2017, 37, 1939(in Chinese).(陈燚,胡奥晗,杨凌毅,李早英,严琨,有机化学,2017,37,1939.)
[4]Bowden, K.; Heilbron, I. M.; Jones, E. R. H.; Weedon, B. C. L. J.Chem. Soc. 1946, 39.
[5]Corey, E. J.; Suggs, J. W. Tetrahedron Lett. 1975, 16, 2647.
[6]Piancatelli, G.; Scettri, A.; Auria, M. Synthesis 1982, 245.
[7]De, A. J. Sci. Ind. Res. 1982, 41, 484.
[8]Luzzio, F. A.; Guziec, F. S. Org. Prep. Proced. Int. 1988, 20, 533.
[9]Ladbury, J. W.; Cullis, C. F. Chem. Rev. 1958, 58, 403.
[10]Fatiadi, A. J. Synthesis 1976, 65.
[11]Taylor,R.J.K.;Reid,M.;Foot,J.;Raw,S.A.Acc.Chem.Res.2005, 38, 851.
[12]Semmelhack,M.F.;Schmid,C.R.;Cortes,D.A.;Chou,C.S.J.Am. Chem. Soc. 1984, 106, 3374.
[13]Gamez,P.;Arends,I.W.C.E.;Sheldon,R.A.;Reedijk,J.Adv.Synth. Catal. 2004, 346, 805.
[14]Jiang, N.; Ragauskas, A. J. J. Org. Chem. 2006, 71, 7087.
[15]Figiel,P.J.;Sibaouih,A.;Ahmad,J.U.;Nieger,M.;Leskela,M.;Repo, T. Adv. Synth. Catal. 2009, 351, 2625.
[16]Konning, D.; Hiller, W.; Christmann, M. Org. Lett. 2012, 14, 5258.
[17]Hoover, J. M.; Steves, J. E.; Stahl, S. S. Nat. Protoc. 2012, 7, 1161.
[18]Ragagnin,G.;Betzemeier,B.;Quici,S.;Knochel,P.Tetrahedron2002, 58, 3985.
[19]Betzemeier,B.Cavazzini,M.;Quici,S.;Knochel,P.Tetrahedron Lett. 2000, 41, 4343.
[20]Ansari, I. A.; Gree, R. Org. Lett. 2002, 4, 1507.
[21]Liu, K. J.; Fu,Y. L.; Xie, L. Y.; Wu, C.; He, W. B.; Peng, S.; Wang,Z.;Bao,W.H.;Cao,Z.;Xu,X.H.;He,W.M.ACSSustainable Chem. Eng. 2018, 6, 4916.
[22]Jiang, X. G.; Zhai, Y. Z.; Chen, J. Y.; Han,Y. L.; Yang, Z.; Ma, S. M.Chin. J. Chem. 2018, 36, 15.
[23]Steves, J. E.; Stahl, S. S. J. Am. Chem. Soc. 2013, 135, 15742.
[24]Gamez, P.; Reedijk, J.; Sheldon, R. A. Chem. Commun. 2003, 2414.
[25]Hoover, J. M.; Stahl, S. S. J. Am. Chem. Soc. 2011, 133, 16901.
[26]Kumpulainen, E. T. T.; Koskinen, A. M. P. Chem.-Eur. J. 2009, 15,10901.
[27]Steves, J. E.; Stahl, S. S. J. Org. Chem. 2015, 80, 11184.
[28]Hill, N. J.; Hoover, J. M.; Stahl, S. S. J. Chem. Educ. 2013, 90, 102.
[29]Hoover, J. M.; Ryland, B. L.; Stahl, S. S. ACS Catal. 2013, 3, 2599.
[30]Corre, Y.; Rysak, V.; Capet, F.; Djukic, J. P.; Agbossou-Niedercorn,F.; Michon, C. Chemistry 2016, 22, 14036.
[31]Zhan, L. W.; Han, L.; Xing, P.; Jiang, B. Chemistry 2016, 47, 5990.