Synlett 2016; 27(10): 1450-1455
DOI: 10.1055/s-0035-1561416
synpacts
© Georg Thieme Verlag Stuttgart · New York

A Massé Shot: Transition-Metal-Catalyzed Selective meta-C–H Functionalization (ortho-Metallation and para-Bromination Relay)

Liu Liu
a   School of Pharmaceutical Science and Technology, Tianjin University, 92 Weijin Road, Nankai District, Tianjin 300072, P. R. of China
,
Qing Wang
a   School of Pharmaceutical Science and Technology, Tianjin University, 92 Weijin Road, Nankai District, Tianjin 300072, P. R. of China
,
Ranran Zhu
a   School of Pharmaceutical Science and Technology, Tianjin University, 92 Weijin Road, Nankai District, Tianjin 300072, P. R. of China
b   Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, P. R. of China
c   Tianjin Key Laboratory for Modern Drug Delivery & High Efficiency, Tianjin 300072, P. R. of China   Email: jhuang@tju.edu.cn
,
Jianhui Huang*
a   School of Pharmaceutical Science and Technology, Tianjin University, 92 Weijin Road, Nankai District, Tianjin 300072, P. R. of China
b   Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, P. R. of China
c   Tianjin Key Laboratory for Modern Drug Delivery & High Efficiency, Tianjin 300072, P. R. of China   Email: jhuang@tju.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 31 December 2015

Accepted after revision: 22 February 2016

Publication Date:
17 March 2016 (online)


Abstract

Reviewed herein are a number of modern approaches for the meta-selective direct C–H functionalization of substituted arenes, including a recent discovery on Ru-catalyzed meta-bromination is also discussed with the mechanistically interesting features (ortho-metallation and para-functionalization relay).

1 Introduction

2 Transition-Metal-Mediated meta-C–H Activation

3 Ruthenium-Catalyzed meta-C–H Bromination

4 Conclusion and Future Directions

 
  • References

    • 1a Ouellet SG, Roy A, Molinaro C, Angelaud R, Marcoux JF, O’Shea PD, Davies IW. J. Org. Chem. 2011; 76: 1436
    • 1b Wang J, Rosingana M, Watson DJ, Discordia RP, Soundarajan N, Li W.-S. Tetrahedron Lett. 2001; 42: 8935
    • 2a Wang GW, Yuan TT, Li DD. Angew. Chem. Int. Ed. 2011; 50: 1380
    • 2b Mei TS, Wang DH, Yu J.-Q. Org. Lett. 2010; 12: 3140
    • 2c Xiao B, Gong TJ, Xu J, Liu ZJ, Liu L. J. Am. Chem. Soc. 2011; 133: 1466
  • 3 Heck R. J. Org. Chem. 1972; 37: 2320
  • 4 Miyaura N, Suzuki A. J. Chem. Soc., Chem. Commun. 1976; 866
  • 5 Baba S, Negishi E. J. Chem. Soc., Chem. Commun. 1976; 596
  • 6 Ullmann F, Bielecki J. Ber. 1901; 34: 2174
    • 7a Guram AS, Buchwald SL. J. Am. Chem. Soc. 1994; 116: 7901
    • 7b Paul F, Patt J, Hartwig JF. J. Am. Chem. Soc. 1994; 116: 5969
    • 8a Liu YJ, Xu H, Kong WJ, Shang M, Dai HX, Yu JQ. Nature (London) 2014; 515: 390
    • 8b Chu L, Xiao KJ, Yu JQ. Science 2014; 346: 451
    • 8c Tang RY, Li G, Yu JQ. Nature (London) 2014; 507: 215
    • 8d Wang DH, Engle KM, Shi BF, Yu JQ. Science 2010; 327: 315
    • 9a Jin J, MacMillan DW. C. Nature (London) 2015; 525: 87
    • 9b Nagib DA, MacMillan DW. C. Nature (London) 2011; 480: 224
    • 9c Jin J, MacMillan DW. C. Angew. Chem. Int. Ed. 2015; 54: 1565
    • 9d Cuthbertson JD, MacMillan DW. C. Nature (London) 2015; 519: 74
    • 10a Duong HA, Gilligan RE, Cooke ML, Phipps RJ, Gaunt MJ. Angew. Chem. Int. Ed. 2010; 50: 463
    • 10b Tredwell MJ, Gulias M, Bremeyer NG, Johansson CC. C, Collins BS. L, Gaunt MJ. Angew. Chem. Int. Ed. 2011; 50: 1076
    • 11a Neufeldt SR, Sanford MS. Acc. Chem. Res. 2012; 45: 936
    • 11b Desai LV, Stowers KJ, Sanford MS. J. Am. Chem. Soc. 2008; 130: 13285
    • 11c Wagner AM, Hickman AJ, Sanford MS. J. Am. Chem. Soc. 2013; 135: 15710
    • 11d Hickman AJ, Sanford MS. Nature (London) 2012; 484: 177
    • 11e Racowski JM, Ball ND, Sanford MS. J. Am. Chem. Soc. 2011; 133: 18022
    • 11f Cook AK, Sanford MS. J. Am. Chem. Soc. 2015; 137: 3109
    • 12a Zhao X, Dimitrijević E, Dong VM. J. Am. Chem. Soc. 2009; 131: 3466
    • 12b Zhao X, Yeung CS, Dong VM. J. Am. Chem. Soc. 2010; 132: 5837
    • 12c Whittaker AM, Dong VM. Angew. Chem. Int. Ed. 2015; 54: 1312
    • 13a Chen X, Engle KM, Wang DH, Yu JQ. Angew. Chem. Int. Ed. 2009; 48: 5094
    • 13b Ackermann L. Acc. Chem. Res. 2014; 47: 281
    • 13c Topczewski JJ, Sanford MS. Chem. Sci. 2015; 6: 70
    • 13d Daugulis O, Do HQ, Shabashov D. Acc. Chem. Res. 2009; 42: 1074
    • 13e Zhang F, Spring DR. Chem. Soc. Rev. 2014; 43: 6906
    • 13f De-Sarkar S, Liu W, Kozhushkov SI, Ackermann L. Adv. Synth. Catal. 2014; 356: 1461
    • 13g Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147
    • 13h Arockiam PB, Bruneau C, Dixneuf PH. Chem. Rev. 2012; 112: 5879
    • 13i Kuhl N, Hopkinson MN, Wencel-Delord J, Glorius F. Angew. Chem. Int. Ed. 2012; 51: 10236
    • 13j Colby DA, Bergman RG, Ellman JA. Chem. Rev. 2010; 110: 624
    • 14a Li J, Sarkar SD, Ackermann L. Top. Organomet. Chem. 2015; 55: 217
    • 14b Bag S, Patra T, Modak A, Deb A, Maity S, Dutta U, Dey A, Kancherla R, Maji A, Hazra A, Bera M, Maiti D. J. Am. Chem. Soc. 2015; 137: 11888
    • 14c Ciana CL, Phipps RJ, Brandt JR, Meyer FM, Gaunt MJ. Angew. Chem. Int. Ed. 2011; 50: 458
    • 15a Cho JY, Tse MK, Holmes D, Maleczka RE, Smith MR. Science 2002; 295: 305
    • 15b Ishiyama T, Takagi J, Ishida K, Miyaura N, Anastasi NR, Hartwig JF. J. Am. Chem. Soc. 2002; 124: 390
    • 16a Leow D, Li G, Mei TS, Yu JQ. Nature (London) 2012; 486: 518
    • 16b Bera M, Maji A, Sahoo SK, Maiti D. Angew. Chem. Int. Ed. 2015; 54: 8515
    • 16c Maji A, Bhaskararao B, Singha S, Sunoj RB, Maiti D. Chem. Sci. 2016; Advance Article, DOI: 10.1039/C5SC04060D
    • 17a Wang XC, Gong W, Fang LZ, Zhu RY, Li S, Engle KM, Yu JQ. Nature (London) 2015; 519: 334
    • 17b Zhe D, Wang J, Dong G. J. Am. Chem. Soc. 2015; 137: 5887
  • 18 Phipps RJ, Gaunt MJ. Science 2009; 323: 1593
    • 19a Saidi O, Marafie J, Ledger AE. W, Liu PM, Mahon MF, Kociok-Kohn G, Whittlesey MK, Frost CG. J. Am. Chem. Soc. 2011; 133: 19298
    • 19b Hofmann N, Ackermann L. J. Am. Chem. Soc. 2013; 135: 5877
    • 19c Vicente R, Hofmann N, Ackermann L. Org. Lett. 2011; 13: 1875
    • 19d Paterson AJ, John-Campbell SS, Mahon MF, Press NJ, Frost CG. Chem. Commun. 2015; 51: 12807
  • 20 Huang J, Yu Q, Hu L, Wang Y, Zhao K. Chin. Patent CN104356053, 2014
    • 21a Yu Q, Hu L, Wang Y, Zheng S, Huang J. Angew. Chem. Int. Ed. 2015; 127: 15284
    • 21b Teskey CJ, Lui AY. W, Greaney MF. Angew. Chem. Int. Ed. 2015; 54: 11677