Nickel-Catalyzed Transformation of Aryl 2-Pyridyl Ethers via Cleavage of the Carbon–Oxygen Bond: Synthesis of Mono-α-arylated­ Ketones

Jing Li; Zhong-Xia Wang

doi:10.1055/s-0037-1609963

Synthesis, Table of Contents

Synthesis 2018; 50(16): 3217-3223
DOI: 10.1055/s-0037-1609963

special topic

Nickel-Catalyzed Transformation of Aryl 2-Pyridyl Ethers via Cleavage of the Carbon–Oxygen Bond: Synthesis of Mono-α-arylated Ketones

Authors

Jing Li

^aCAS Key Laboratory of Soft Matter Chemistry, Hefei National Laboratory for Physical Sciences at Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P. R. of China
Zhong-Xia Wang *

^aCAS Key Laboratory of Soft Matter Chemistry, Hefei National Laboratory for Physical Sciences at Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P. R. of China

^bCollaborative Innovation Center of Chemical Science and Engineering, Tianjin 300072, P. R. of China Email: zxwang@ustc.edu.cn

Abstract

All articles of this category

Published as part of the Special Topic Modern Coupling Approaches and their Strategic Applications in Synthesis

Abstract

The nickel/IPr-catalyzed reaction of aryl 2-pyridyl ethers with propiophenone and acetophenone derivatives via C–OPy bond cleavage is performed in the presence of t-BuOLi to give mono-α-arylated ketones in moderate yields. The method is suitable for electron-rich and electron-poor ethers as well as heteroaryl ethers and tolerates a range of active functional groups.

Key words

aryl 2-pyridyl ethers - C–O activation - C–C coupling - nickel catalyst - α-arylated ketones

Full Text

References

References

1a Rosen BM. Quasdorf KW. Wilson DA. Zhang N. Resmerita A.-M. Garg NK. Percec V. Chem. Rev. 2011; 111: 1346
1b Mesganaw T. Garg NK. Org. Process Res. Dev. 2013; 17: 29
1c Gooßen LJ. Gooßen K. Stanciu C. Angew. Chem. Int. Ed. 2009; 48: 3569
1d Li B.-J. Yu D.-G. Sun C.-L. Shi Z.-J. Chem. Eur. J. 2011; 17: 1728
1e Han F.-S. Chem. Soc. Rev. 2013; 42: 5270

2a Kinuta H. Tobisu M. Chatani N. J. Am. Chem. Soc. 2015; 137: 1593
2b Tobisu M. Zhao J. Kinuta H. Furukawa T. Igarashi T. Chatani N. Adv. Synth. Catal. 2016; 358: 2417
2c Li J. Wang Z.-X. Org. Lett. 2017; 19: 3723
2d Li J. Wang Z.-X. Chem. Commun. 2018; 54: 2138

3a Kakiuchi F. Igi K. Matsumoto M. Hayamizu T. Chatani N. Murai S. Chem. Lett. 2002; 31: 396
3b Ackermann L. Diers E. Manvar A. Org. Lett. 2012; 14: 1154
3c Niu L. Yang H. Wang R. Fu H. Org. Lett. 2012; 14: 2618
3d Yao J. Feng R. Wu Z. Liu Z. Zhang Y. Adv. Synth. Catal. 2013; 355: 1517
3e Liang Y.-F. Li X. Wang X. Yan Y. Feng P. Jiao N. ACS Catal. 2015; 5: 1956
3f Lou S.-J. Chen Q. Wang Y.-F. Xu D.-Q. Du X.-H. He J.-Q. Mao Y.-J. Xu Z.-Y. ACS Catal. 2015; 5: 2846
3g Chu J.-H. Lin P.-S. Wu M.-J. Organometallics 2010; 29: 4058

4a Wright WB. Jr. Press JB. Chan PS. Marsico JW. Haug MF. Lucas J. Tauber J. Tomcufcik AS. J. Med. Chem. 1986; 29: 523
4b Goehring RR. Sachdeva YP. Pisipati JS. Sleevi MC. Wolfe JF. J. Am. Chem. Soc. 1985; 107: 435
4c Venkatesan H. Davis MC. Altas Y. Snyder JP. Liotta DC. J. Org. Chem. 2001; 66: 3653
4d Johansson CC. C. Colacot TJ. Angew. Chem. Int. Ed. 2010; 49: 676

5a Satoh T. Kawamura Y. Miura M. Nomura M. Angew. Chem. Int. Ed. 1997; 36: 1740
5b Palucki M. Buchwald SL. J. Am. Chem. Soc. 1997; 119: 11108
5c Hamann BC. Hartwig JF. J. Am. Chem. Soc. 1997; 119: 12382
5d Bellina F. Rossi R. Chem. Rev. 2010; 110: 1082
5e Li J. Wang Z.-X. Org. Biomol. Chem. 2016; 14: 7579

6a Marelli E. Davies M. Nolan SP. Chem. Eur. J. 2014; 20: 17272
6b Viciu MS. Germaneau RF. Nolan SP. Org. Lett. 2002; 4: 4053
6c Liao X. Weng Z. Hartwig JF. J. Am. Chem. Soc. 2008; 130: 195
6d Nguyen HN. Huang X. Buchwald SL. J. Am. Chem. Soc. 2003; 125: 11818
6e Hesp KD. Lundgren RJ. Stradiotto M. J. Am. Chem. Soc. 2011; 133: 5194
6f Ackermann L. Mehta VP. Chem. Eur. J. 2012; 18: 10230
6g Alsabeh PG. Stradiotto M. Angew. Chem. Int. Ed. 2013; 52: 7242

7a Takise R. Muto K. Yamaguchi J. Itami K. Angew. Chem. Int. Ed. 2014; 53: 6791
7b Cornella J. Jackson EP. Martin R. Angew. Chem. Int. Ed. 2015; 54: 4075

8a Matsubara K. Ueno K. Koga Y. Hara K. J. Org. Chem. 2007; 72: 5069
8b Fernández-Salas JA. Marelli E. Cordes DB. Slawin AM. Z. Nolan SP. Chem. Eur. J. 2015; 21: 3906
8c Henrion M. Chetcuti MJ. Ritleng V. Chem. Commun. 2014; 50: 4624
8d Grigalunas M. Ankner T. Norrby P.-O. Wiest O. Helquist P. J. Am. Chem. Soc. 2015; 137: 7019

9 Fujimoto T. Ritter T. Org. Lett. 2015; 17: 544
10 Grasa GA. Colacot TJ. Org. Lett. 2007; 9: 5489
11 Drapeau MP. Fabre I. Grimaud L. Ciofini I. Ollevier T. Taillefer M. Angew. Chem. Int. Ed. 2015; 54: 10587
12 Hong Y.-T. Barchuk A. Krische MJ. Angew. Chem. Int. Ed. 2006; 45: 6885
13 Mendoza-Espinosa D. González-Olvera R. Negrón-Silva GE. Angeles-Beltrán D. Suárez-Castillo OR. Álvarez-Hernández A. Santillan R. Organometallics 2015; 34: 4529
14 Marelli E. Renault Y. Sharma SV. Nolan SP. Goss RJ. M. Chem. Eur. J. 2017; 23: 3832
15 Deng Z. Chen C. Cui S. RSC Adv. 2016; 6: 93753
16 Speckmeier E. Padié C. Zeitler K. Org. Lett. 2015; 17: 4818
17 Purohit VC. Allwein SP. Bakale RP. Org. Lett. 2013; 15: 1650

Supplementary Material

Supporting Information (PDF)

Nickel-Catalyzed Transformation of Aryl 2-Pyridyl Ethers via Cleavage of the Carbon–Oxygen Bond: Synthesis of Mono-α-arylated­ Ketones

Authors

Nickel-Catalyzed Transformation of Aryl 2-Pyridyl Ethers via Cleavage of the Carbon–Oxygen Bond: Synthesis of Mono-α-arylated Ketones