Palladium-Catalyzed Reductive Coupling of Nitroarenes with Phenols­ leading to N-Cyclohexylanilines

Kai-Jian Liu; Xiu-Ling Zeng; Yong Zhang; Yi Wang; Xin-Sheng Xiao; Huilan Yue; Ming Wang; Zilong Tang; Wei-Min He

doi:10.1055/s-0037-1610231

Synthesis, Table of Contents

Synthesis 2018; 50(23): 4637-4644
DOI: 10.1055/s-0037-1610231

paper

Palladium-Catalyzed Reductive Coupling of Nitroarenes with Phenols leading to N-Cyclohexylanilines

Kai-Jian Liu

^aHunan Provincial Engineering Research Center for Ginkgo biloba, Hunan University of Science and Engineering, Yongzhou 425100, P. R. of China Email: weiminhe2016@yeah.net

,

Xiu-Ling Zeng

^aHunan Provincial Engineering Research Center for Ginkgo biloba, Hunan University of Science and Engineering, Yongzhou 425100, P. R. of China Email: weiminhe2016@yeah.net

,

Yong Zhang

^aHunan Provincial Engineering Research Center for Ginkgo biloba, Hunan University of Science and Engineering, Yongzhou 425100, P. R. of China Email: weiminhe2016@yeah.net

,

Yi Wang

^aHunan Provincial Engineering Research Center for Ginkgo biloba, Hunan University of Science and Engineering, Yongzhou 425100, P. R. of China Email: weiminhe2016@yeah.net

,

Xin-Sheng Xiao

^aHunan Provincial Engineering Research Center for Ginkgo biloba, Hunan University of Science and Engineering, Yongzhou 425100, P. R. of China Email: weiminhe2016@yeah.net

,

Huilan Yue

^bKey Laboratory of Tibetan Medicine Research, Northwest Institute of Plateau Biology, Chinese Academy of Sciences and Qinghai Provincial Key Laboratory of Tibetan Medicine Research, Qinghai 810008, P. R. of China

,

Ming Wang

^cKey Laboratory of Theoretical Organic Chemistry and Functional Molecule of Ministry of Education, Hunan University of Science and Technology, Xiangtan 411201, P. R. of China

,

Zilong Tang

^cKey Laboratory of Theoretical Organic Chemistry and Functional Molecule of Ministry of Education, Hunan University of Science and Technology, Xiangtan 411201, P. R. of China

,

Wei-Min He *

^aHunan Provincial Engineering Research Center for Ginkgo biloba, Hunan University of Science and Engineering, Yongzhou 425100, P. R. of China Email: weiminhe2016@yeah.net

› Author Affiliations

Abstract

All articles of this category

Abstract

A direct and efficient palladium-catalyzed reductive coupling reaction of nitroarenes with phenols has been developed. A series of N-cyclohexylaniline derivatives was easily and efficiently obtained in moderate to good yields via C–N bond formation by the simple use of safe and inexpensive sodium formate as the hydrogen donor.

Key words

green chemistry - palladium catalysis - reductive coupling - nitroarene - phenol - cyclohexylamine

Full Text

References

References and Notes

1a Rylander PN. Hydrogenation Methods . Academic; London: 1985: 104-117
1b Nishimura S. Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis. Wiley; New York: 2001: 315-387

2a Adams JP. Paterson JR. J. Chem. Soc., Perkin Trans. 1 2000; 3695
2b Lawrence SA. Amines: Synthesis Properties and Applications . Cambridge University Press; Cambridge: 2004
2c Corma A. Serna P. Science (Washington, D. C.) 2006; 313: 332
2d Ono N. The Nitro Group in Organic Synthesis . Wiley-VCH; New York: 2011

3a Xiao F. Liu Y. Tang C. Deng G.-J. Org. Lett. 2012; 14: 984
3b Pereira MF. Thiéry V. Org. Lett. 2012; 14: 4754
3c Nguyen TB. Ermolenko L. Al-Mourabit A. Org. Lett. 2013; 15: 4218
3d Wang H. Cao X. Xiao F. Liu S. Deng G.-J. Org. Lett. 2013; 15: 4900
3e Wen J. Wei W. Xue S. Yang D. Lou Y. Gao C. Wang H. J. Org. Chem. 2015; 80: 4966
3f Imrich H.-G. Conrad J. Bubrin D. Beifuss U. J. Org. Chem. 2015; 80: 2319
3g Cui H. Wei W. Yang D. Zhang J. Xu Z. Wen J. Wang H. RSC Adv. 2015; 5: 84657
3h Zhao F. Li B. Huang H. Deng G.-J. RSC Adv. 2016; 6: 13010

4a Magano J. Dunetz JR. Chem. Rev. 2011; 111: 2177
4b Ricci A. Amino Group Chemistry: From Synthesis to the Life Sciences. Wiley-VCH; Weinheim: 2008
4c Wei W. Wen J. Yang D. Sun X. You J. Suo Y. Wang H. Tetrahedron 2013; 69: 10747
4d Wei W. Wen J. Yang D. Du J. You J. Wang H. Green Chem. 2014; 16: 2988
4e Wei W. Wen J. Yang D. Liu X. Guo M. Dong R. Wang H. J. Org. Chem. 2014; 79: 422
4f Wei W. Cui H. Yang D. Yue H. He C. Zhang Y. Wang H. Green Chem. 2017; 19: 5608

5 Deng G. Chen W. Li C.-J. Adv. Synth. Catal. 2009; 351: 353

6a Yamane Y. Liu X. Hamasaki A. Ishida T. Haruta M. Yokoyama T. Tokunaga M. Org. Lett. 2009; 11: 5162
6b Sreedhar B. Reddy P. Devi D. J. Org. Chem. 2009; 74: 8806

7a Feng C. Liu Y. Peng S. Shuai Q. Deng G. Li C.-J. Org. Lett. 2010; 12: 4888
7b Liu Y. Chen W. Feng C. Deng G. Chem. Asian J. 2011; 6: 1142
7c Gelman F. Blum J. Avnir D. New J. Chem. 2003; 27: 205
7d Tang C.-H. He L. Liu Y.-M. Cao Y. He H.-Y. Fan K.-N. Chem. Eur. J. 2011; 17: 7172

8a Xie Y. Liu S. Liu Y. Wen Y. Deng G.-J. Org. Lett. 2012; 14: 1692
8b Sutter M. Duclos M.-C. Guicheret B. Raoul Y. Metay E. Lemaire M. ACS Sustainable Chem. Eng. 2013; 1: 1463
8c Wei W. Wen J. Yang D. Guo M. Wang Y. You J. Wang H. Chem. Commun. 2015; 51: 768

9a Upton BM. Kasko AM. Chem. Rev. 2016; 116: 2275
9b Li C. Zhao X. Wang A. Huber GW. Zhang T. Chem. Rev. 2015; 115: 11559
9c Huber GW. Corma A. Angew. Chem. Int. Ed. 2007; 46: 7184

10a Su B. Cao Z.-C. Shi Z.-J. Acc. Chem. Res. 2015; 48: 886
10b Tobisu M. Chatani N. Acc. Chem. Res. 2015; 48: 1717
10c Tobisu M. Morioka T. Ohtsuki A. Chatani N. Chem. Sci. 2015; 6: 3410
10d Zarate C. Manzano R. Martin R. J. Am. Chem. Soc. 2015; 137: 6754
10e Cornella J. Zarate C. Martin R. Chem. Soc. Rev. 2014; 43: 8081
10f Tasker SZ. Standley EA. Jamison TF. Nature (London) 2014; 509: 299
10g Chen Z. Zeng H. Gong H. Wang H. Li C.-J. Chem. Sci. 2015; 6: 4174
10h Chen Z. Zeng H. Girard SA. Wang F. Chen N. Li C.-J. Angew. Chem. Int. Ed. 2015; 54: 14487
10i Jumde VR. Petricci E. Petrucci C. Santillo N. Taddei M. Vaccaro L. Org. Lett. 2015; 17: 3990
10j Meng Q. Hou M. Liu H. Song J. Han B. Nat. Commun. 2017; 8: 14190
10k Qiu Z. Li J.-S. Li C.-J. Chem. Sci. 2017; 8: 6954
10l Bisz E. Szostak M. ChemSusChem 2017; 10: 3964

11 Entwistle ID. Jackson AE. Johnstone RA. W. Telford RP. J. Chem. Soc., Perkin Trans. 1 1977; 443

12a Li W. Yin G. Huang L. Xiao Y. Fu Z. Xin X. Liu F. Li Z. He W. Green Chem. 2016; 18: 4879
12b Wu C. Xin X. Fu Z.-M. Xie L.-Y. Liu K.-J. Wang Z. Li W. Yuan Z.-H. He W.-M. Green Chem. 2017; 19: 1983
12c Xie L.-Y. Duan Y. Lu L.-H. Li Y.-J. Peng S. Wu C. Liu K.-J. Wang Z. He W.-M. ACS Sustainable Chem. Eng. 2017; 5: 10407
12d Xie L.-Y. Li Y.-J. Qu J. Duan Y. Hu J. Liu K.-J. Cao Z. He W.-M. Green Chem. 2017; 19: 5642
12e 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. He W.-M. ACS Sustainable Chem. Eng. 2018; 6: 4916
12f Liu K.-J. Jiang S. Lu L.-H. Tang L.-L. Tang S.-S. Tang H.-S. Tang Z. He W.-M. Xu X. Green Chem. 2018; 20: 3038
12g Wu C. Wang Z. Hu Z. Zeng F. Zhang X.-Y. Cao Z. Tang Z. He W.-M. Xu X.-H. Org. Biomol. Chem. 2018; 16: 3177
12h Wu C. Wang J. Zhang X.-Y. Jia G.-K. Cao Z. Tang Z. Yu X. Xu X. He W.-M. Org. Biomol. Chem. 2018; 16: 5050
12i Xie L.-Y. Qu J. Peng S. Liu K.-J. Wang Z. Ding M.-H. Wang Y. Cao Z. He W.-M. Green Chem. 2018; 20: 760
12j Wu C. Lu L.-H. Peng A.-Z. Jia G.-K. Peng C. Cao Z. Tang Z. He W.-M. Xu X. Green Chem. 2018; 20: 3686
12k Xie L.-Y. Peng S. Lu L.-H. Hu J. Bao W.-H. Zeng F. Tang Z. Xu X. He W.-M. ACS Sustainable Chem. Eng. 2018; 6: 7989

13 Rajagopal S. Spatola AF. J. Org. Chem. 1995; 60: 1347

For selected examples of reduction of phenols, see:

14a Liu H. Jiang T. Han B. Liang S. Zhou Y. Science (Washington, D. C.) 2009; 326: 1250
14b Zhu J.-F. Tao G.-H. Liu H.-Y. He L. Sun Q.-H. Liu H.-C. Green Chem. 2014; 16: 2664
14c Wang Y. Yao J. Li H. Su D. Antonietti M. J. Am. Chem. Soc. 2011; 133: 2362
14d Makowski P. Cakan RD. Antonietti M. Goettmann F. Titirici MM. Chem. Commun. 2008; 999
14e Li Y. Xu X. Zhang P. Gong Y. Li H. Wang Y. RSC Adv. 2013; 3: 10973
14f Chen A. Li Y. Chen J. Zhao G. Ma L. Yu Y. ChemPlusChem 2013; 78: 1370

For reviews on the catalytic reduction of imines, see:

15a Xie J.-H. Zhu S.-F. Zhou Q.-L. Chem. Rev. 2011; 111: 1713
15b Kobayashi S. Ishitani H. Chem. Rev. 1999; 99: 1069

Supplementary Material

Supporting Information

Palladium-Catalyzed Reductive Coupling of Nitroarenes with Phenols­ leading to N-Cyclohexylanilines

Palladium-Catalyzed Reductive Coupling of Nitroarenes with Phenols leading to N-Cyclohexylanilines