Efficient Catalyst-Free Henry Reaction between Nitroalkanes and Aldehydes or Trifluoromethyl Ketones Promoted by Tap Water

Zhi-Hong Du; Meng Yuan; Bao-Xiu Tao; Tie-Ying Ding; Chao-Shan Da

doi:10.1055/a-1933-3709

Synthesis, Inhaltsverzeichnis

Synthesis 2022; 54(24): 5461-5470
DOI: 10.1055/a-1933-3709

paper

Efficient Catalyst-Free Henry Reaction between Nitroalkanes and Aldehydes or Trifluoromethyl Ketones Promoted by Tap Water

Zhi-Hong Du ∗

^aSchool of Chemistry and Chemical Engineering, The Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University, Xinjiang 832003, P. R. of China

,

Meng Yuan

^bInstitute of Biochemistry and Molecular Biology, School of Life Sciences, State Key Laboratory of Applied Organic Chemistry, Key Lab of Preclinical Study for New Drugs of Gansu Province, Lanzhou University, Lanzhou 730000, P. R. of China

,

Bao-Xiu Tao

^bInstitute of Biochemistry and Molecular Biology, School of Life Sciences, State Key Laboratory of Applied Organic Chemistry, Key Lab of Preclinical Study for New Drugs of Gansu Province, Lanzhou University, Lanzhou 730000, P. R. of China

,

Tie-Ying Ding

^bInstitute of Biochemistry and Molecular Biology, School of Life Sciences, State Key Laboratory of Applied Organic Chemistry, Key Lab of Preclinical Study for New Drugs of Gansu Province, Lanzhou University, Lanzhou 730000, P. R. of China

,

Chao-Shan Da ∗

^bInstitute of Biochemistry and Molecular Biology, School of Life Sciences, State Key Laboratory of Applied Organic Chemistry, Key Lab of Preclinical Study for New Drugs of Gansu Province, Lanzhou University, Lanzhou 730000, P. R. of China

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Abstract

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Abstract

The first examples of highly effective Henry reactions between nitroalkanes and aldehydes or trifluoromethyl ketones that proceed under catalyst-free and additive-free conditions, in a recyclable tap water medium, and at room temperature are reported. This process tolerates a broad range of aldehydes and trifluoromethyl ketones to give a series of β-nitro alcohol products in excellent yields. Such products are widely used in the syntheses of pharmaceutical intermediates and natural products. This protocol can be successfully scaled up to a 50-mmol scale without a reduction in yield. Tap water from different locations in China exhibited pH values ranging from 7.5 to 8.1, but the varying pH had no effect on the yield and the processes were successfully reproduced. Finally, the tap water was effectively recovered and reused without any postprocessing, even when the reaction substrates were different.

Key words

tap water - green synthesis - catalyst free - Henry reaction - trifluoromethyl ketones

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Referenzen

References

For recent reviews on green chemistry, see:

1a Zimmerman JB, Anastas PT, Erythropel HC, Leitner W. Science 2020; 367: 397
1b Anastas P, Eghbali N. Chem. Soc. Rev. 2010; 39: 301
1c Horváth IT, Anastas PT. Chem. Rev. 2007; 107: 2167

For recent reviews about organic reactions in water or on water, see:

2a Kitanosono T, Kobayashi S. Chem. Eur. J. 2020; 26: 9408
2b Zhou F, Li C.-J. Chem. Sci. 2019; 10: 34
2c Butler RN, Coyne AG. Chem. Rev. 2010; 110: 6302
2d Chanda A, Fokin VV. Chem. Rev. 2009; 109: 725
2e Blackmond DG, Armstrong A, Coombe V, Wells A. Angew. Chem. Int. Ed. 2007; 46: 3798
2f Hayashi Y. Angew. Chem. Int. Ed. 2006; 45: 8103
2g Li C.-J. Chem. Rev. 2005; 105: 3095
2h Lai G, Guo F, Zheng Y, Fang Y, Song H, Xu K, Wang S, Zha Z, Wang Z. Chem. Eur. J. 2011; 17: 1114

3 Andraos J. Org. Process Res. Dev. 2012; 16: 1482

References about tap water used as a reaction medium are sporadic; see:

4a Tang BZ, Poon WH, Leung SM, Leung WH, Peng H. Macromolecules 1997; 30: 2209
4b Wang Z, Zha Z, Zhou C. Org. Lett. 2002; 4: 1683
4c SaiPrathima P, Srinivas K, Rao MM. Green Chem. 2015; 17: 2339
4d Nagaraju S, Satyanarayana N, Paplal B, Vasu AK, Kanvah S, Kashinath D. RSC Adv. 2015; 5: 81768
4e Kumar N, Kaur J, Kumar A, Islam N, Chimni SS. Asian J. Org. Chem. 2016; 5: 1334

For references on nitro alcohol utility in organic synthesis, see:

5a Rao DH. S, Chatterjee A, Padhi SK. Org. Biomol. Chem. 2021; 19: 322
5b Zlotin SG, Dalinger IL, Makhova NN, Tartakovsky VA. Russ. Chem. Rev. 2020; 89: 1
5c Pankaj G, Neha M. New J. Chem. 2018; 42: 12296
5d Métro T.-X, Duthion B, Pardo DG, Cossy J. Chem. Soc. Rev. 2010; 39: 89
5e Klingler FD. Acc. Chem. Res. 2007; 40: 1367

For recent reviews on the Henry reaction, see:

6a Luzzio FA. Tetrahedron 2001; 57: 915
6b Palomo C, Oiarbide M, Laso A. Eur. J. Org. Chem. 2007; 2561
6c Ballini R, Barboni L, Fringuelli F, Palmieri A, Pizzo F, Vaccaro L. Green Chem. 2007; 9: 823
6d Milner SE, Moody TS, Maguire AR. Eur. J. Org. Chem. 2012; 3059
6e Murugavel G, Sadhu P, Punniyamurthy T. Chem. Rec. 2016; 16: 1906
6f Saranya S, Harry NA, Ujwaldev SM, Anilkumar G. Asian J. Org. Chem. 2017; 6: 1349
6g Zhang S, Li Y, Xu Y, Wang Z. Chin. Chem. Lett. 2018; 29: 873
6h Dong L, Chen F.-E. RSC Adv. 2020; 10: 2313
6i Cirujano FG, Luque R, Dhakshinamoorthy A. Molecules 2021; 26: 1445
6j Das D, Pathak G, Rokhum L. RSC Adv. 2016; 6: 104154

7a Zhang Y, Wei BW, Lin H, Zhang L, Liu JX, Luo HQ, Fan XL. Green Chem. 2015; 17: 3266
7b Yamada T, Kuwata M, Takakura R, Monguchi Y, Sajiki H, Sawama Y. Adv. Synth. Catal. 2018; 360: 637

8a Ballini R, Bosica G. J. Org. Chem. 1997; 62: 425
8b Ballini R, Fiorini D, Gil MV, Palmieri A. Tetrahedron 2004; 60: 2799

9 Bora PP, Bez G. Eur. J. Org. Chem. 2013; 2922

For references on macrobiomolecules as catalysts to promote aqueous Henry reactions, see:

10a Fan J, Sun G, Wan C, Wang Z, Li Y. Chem. Commun. 2008; 3792
10b Busto E, Gotor-Fernández V, Gotor V. Org. Process Res. Dev. 2011; 15: 236
10c Le ZG, Guo LT, Jiang GF, Yang XB, Liu HQ. Green Chem. Lett. Rev. 2013; 6: 277
10d Gao N, Chen LY, He YH, Guan Z. RSC Adv. 2013; 3: 16850
10e Matsumoto K, Asakura S. Tetrahedron Lett. 2014; 55: 6919
10f Häring M, Pérez-Madrigal MM, Kühbeck D, Pettignano A, Quignard F, Díaz Díaz D. Molecules 2015; 20: 4136
10g Häring M, Pettignano A, Quignard F, Tanchoux N, Díaz Díaz D. Molecules 2016; 21: 1122
10h Tian X, Zhang S, Zheng L. J. Microbiol. Biotechnol. 2016; 26: 80

For references on metal complexes as catalysts to promote aqueous Henry reactions, see:

11a Reddy KR, Rajasekhar CV, Krishna GG. Synth. Commun. 2007; 37: 1971
11b Jammi S, Punniyamurthy T. Eur. J. Inorg. Chem. 2009; 2508
11c Karmakar A, Hazra S, da Silva MF. C. G, Pombeiro AJ. L. New J. Chem. 2014; 38: 4837
11d Karmakar A, Hazra S, da Silva MF. C. G, Paul A, Pombeiro AJ. L. CrystEngComm 2016; 18: 1337

For recent references on application of trifluoromethyl tert-alcohol containing compounds in drugs, see:

12a Ducharme Y, Blouin M, Brideau C, Chateauneuf A, Gareau Y, Grimm EL, Juteau H, Laliberte S, MacKay B, Massé F, Ouellet M, Salem M, Styhler A, Friesen RW. ACS Med. Chem. Lett. 2010; 1: 170
12b Handlon AL, Schaller LT, Leesnitzer LM, Merrihew RV, Poole C, Ulrich JC, Wilson JW, Cadilla R, Turnbull P. ACS Med. Chem. Lett. 2016; 7: 83
12c Ng RA, Lanter JC, Alford VC, Allan GF, Sbriscia T, Lundeen SG, Sui Z. Bioorg. Med. Chem. Lett. 2007; 17: 1784
12d Ozoe Y, Asahi M, Ozoe F, Nakahira K, Mita T. Biochem. Biophys. Res. Commun. 2010; 391: 744
12e Wang H, Yang K.-F, Li L, Bai Y, Zheng Z.-J, Zhang W.-Q, Gao Z.-W, Xu L.-W. ChemCatChem 2014; 6: 580
12f Kasztelan A, Biedrzycki M, Kwiatkowski P. Adv. Synth. Catal. 2016; 358: 2962
12g Zheng Y, Ma H, Ma J.-A. Chin. J. Chem. 2016; 34: 511
12h Wang P, Li H.-F, Zhao J.-Z, Du Z.-H, Da C.-S. Org. Lett. 2017; 19: 2634
12i Thomson CJ, Barber DM, Dixon DJ. Angew. Chem. Int. Ed. 2020; 59: 5359

For recent references on nitroalkane addition to trifluoromethyl ketones, see:

13a Tur F, Saá JM. Org. Lett. 2007; 9: 5079
13b Bandini M, Sinisi R, Umani-Ronchi A. Chem. Commun. 2008; 4360
13c Saá JM, Tur F, González J. Chirality 2009; 21: 836
13d Xu HH, Wolf C. Chem. Commun. 2010; 46: 8026
13e Palacio C, Connon SJ. Org. Lett. 2011; 13: 1298
13f Vlatković M, Bernardi L, Otten E, Feringa BL. Chem. Commun. 2014; 50: 7773
13g Das A, Choudhary MK, Kureshy RI, Jana K, Verma S, Khan NH, Abdi SH. R, Bajaj HC, Ganguly B. Tetrahedron 2015; 71: 5229
13h Karasawa T, Kumagai N, Shibasaki M. Org. Lett. 2018; 20: 308
13i Otevrel J, Svestka D, Bobal P. Org. Biomol. Chem. 2019; 17: 5244
13j Meng X, Luo Y, Zhao G. Tetrahedron Lett. 2020; 61: 152485

14 Baruaha B, Deb ML. Org. Biomol. Chem. 2021; 19: 1191
15 Panov I, Drabina P, Hanusek J, Sedlák M. Synlett 2013; 24: 1280
16 Gogoi N, Boruwa J, Barua NC. Tetrahedron Lett. 2005; 46: 7581

17a Blay G, Domingo LR, Hernández-Olmos V, Pedro JR. Chem. Eur. J. 2008; 14: 4725
17b Otevrel J, Bobal P. J. Org. Chem. 2017; 82: 8342

18 Hayashi K, Watanabe T, Toyama K, Kamon J, Minami M, Uni M, Nasu M. (Nissan Chemical Industries, Ltd.) WO 2013024895, 2013; 158, 359769
19 Tang L.-W, Zhao B.-J, Dai L, Zhang M, Zhou Z.-M. Chem. Asian J. 2016; 11: 2470

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