Synthesis 2017; 49(06): 1150-1157
DOI: 10.1055/s-0036-1588365
short review
© Georg Thieme Verlag Stuttgart · New York

Recent Advances in Dual Visible Light Photoredox and Gold-Catalyzed­ Reactions

Min Zhang
a  School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang 212013, P. R. of China
,
Chunyin Zhu*
a  School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang 212013, P. R. of China
b  State Key Laboratory of Physical Chemistry of Solid Surfaces, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, P. R. of China   Email: [email protected]   Email: [email protected]
,
Long-Wu Ye*
b  State Key Laboratory of Physical Chemistry of Solid Surfaces, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, P. R. of China   Email: [email protected]   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 26 September 2016

Accepted after revision: 04 November 2016

Publication Date:
09 December 2016 (online)


Abstract

In a dual visible light photoredox and gold catalysis system, Au(I) is oxidized in a stepwise fashion by photogenerated aryl radicals leading to cationic Au(III) species, a process which is incorporated into various domino functionalization/coupling reactions. This article presents an overview of the major contributions reported in this field, emphasizing those involving aryldiazonium or diaryliodonium salts as general radical sources.

1 Introduction

2 Domino Nucleophilic Addition/Arylation

3 Domino Rearrangement/Arylation

4 Cross-Coupling

5 Conclusion

 
  • References

    • 1a Nicewicz DA, MacMillan DW. C. Science 2008; 322: 77
    • 1b Ischay MA, Anzovino ME, Du J, Yoon TP. J. Am. Chem. Soc. 2008; 130: 12886
    • 1c Narayanam JM. R, Tucker JW, Stephenson CR. J. J. Am. Chem. Soc. 2009; 131: 8756
    • 1d Nagib DA, Scott ME, MacMillan DW. C. J. Am. Chem. Soc. 2009; 131: 10875

      For selected reviews on photoredox catalysis, see:
    • 2a Xuan J, Xiao WJ. Angew. Chem. Int. Ed. 2012; 51: 6828
    • 2b Prier CK, Rankic DA, MacMillan DW. C. Chem. Rev. 2013; 113: 5322
    • 2c Schultz DM, Yoon TP. Science 2014; 343: 1239176
    • 2d Angnes RA, Li Z, Correia CR. D, Hammond GB. Org. Biomol. Chem. 2015; 13: 9152
    • 2e Xuan J, Zhang ZG, Xiao WJ. Angew. Chem. Int. Ed. 2015; 54: 15632
    • 2f Luo J, Zhang J. ACS Catal. 2016; 6: 873
    • 2g Chen JR, Hu XQ, Lu LQ, Xiao WJ. Chem. Soc. Rev. 2016; 45: 2044
    • 2h Lang X, Zhao J, Chen X. Chem. Soc. Rev. 2016; 45: 3026

      For recent examples on photoredox catalysis, see:
    • 3a Jeffrey JL, Terrett JA, MacMillan DW. C. Science 2015; 349: 1523
    • 3b Douglas JJ, Albright H, Sevrin MJ, Cole KP, Stephenson CR. J. Angew. Chem. Int. Ed. 2015; 54: 14898
    • 3c Zhang G, Liu C, Yi H, Meng Q, Bian C, Chen H, Jian JX, Wu LZ, Lei A. J. Am. Chem. Soc. 2015; 137: 9273
    • 3d Jiang H, An X, Tong K, Zheng T, Zhang Y, Yu S. Angew. Chem. Int. Ed. 2015; 54: 4055
    • 3e Liu C, Oblak EZ, Vander Wal MN, Dilger AK, Almstead DK, MacMillan DW. C. J. Am. Chem. Soc. 2016; 138: 2134
    • 3f Hu XQ, Qi X, Chen J.-R, Zhao QQ, Wei Q, Lan Y, Xiao WJ. Nat. Commun. 2016; 7: 11188
    • 3g Wei Y, Lu LQ, Li TR, Feng B, Wang Q, Xiao WJ, Alper H. Angew. Chem. Int. Ed. 2016; 55: 2200
    • 3h Kainz QM, Matier CD, Bartoszewicz A, Zultanski SL, Peters JC, Fu GC. Science 2016; 351: 681
    • 3i Yayla HG, Peng F, Mangion IK, McLaughlin MM, Campeau LC, Davies IW, DiRocco DA, Knowles RR. Chem. Sci. 2016; 7: 2066
    • 3j Zhong JJ, Liu Q, Wu CJ, Meng QY, Gao XW, Li ZJ, Chen B, Tung CH, Wu LZ. Chem. Commun. 2016; 52: 1800
    • 3k Amador AG, Yoon TP. Angew. Chem. Int. Ed. 2016; 55: 2304
    • 3l Ding Y, Zhang T, Chen Q.-Y, Zhu C. Org. Lett. 2016; 18: 4206
    • 3m Sun X, Wang W, Li Y, Ma J, Yu S. Org. Lett. 2016; 18: 4638
    • 3n Sun X, Yu S. Chem. Commun. 2016; 52: 10898

      For recent reviews on gold catalysis, see:
    • 4a Special issue devoted to gold catalysis: Acc. Chem. Res. 2014; 47: 729
    • 4b Dorel R, Echavarren AM. Chem. Rev. 2015; 115: 9028
    • 4c Qian D, Zhang J. Chem. Soc. Rev. 2015; 44: 677
    • 4d Jia M, Bandini M. ACS Catal. 2015; 5: 1638
    • 4e Wei F, Song C, Ma Y, Zhou L, Tung C.-H, Xu Z. Sci. Bull. 2015; 60: 1479
    • 4f Liu L, Zhang J. Chem. Soc. Rev. 2016; 45: 506
    • 4g Pflästerer D, Hashmi AS. K. Chem. Soc. Rev. 2016; 45: 1331
    • 4h Asiria AM, Hashmi AS. K. Chem. Soc. Rev. 2016; 45: 4471
    • 4i Zheng Z, Wang Z, Wang Y, Zhang L. Chem. Soc. Rev. 2016; 45: 4448
    • 4j Wei Y, Shi M. ACS Catal. 2016; 6: 2515
    • 4k Day DP, Chan PW. H. Adv. Synth. Catal. 2016; 358: 1368

      For selected recent contributions on gold catalysis, see:
    • 5a Kirillova MS, Muratore ME, Dorel R, Echavarren AM. J. Am. Chem. Soc. 2016; 138: 3671
    • 5b Hosseyni S, Wojtas L, Li M, Shi X. J. Am. Chem. Soc. 2016; 138: 3994
    • 5c Ding D, Mou T, Feng M, Jiang X. J. Am. Chem. Soc. 2016; 138: 5218
    • 5d Jin H, Huang L, Xie J, Rudolph M, Rominger F, Hashmi AS. K. Angew. Chem. Int. Ed. 2016; 55: 794
    • 5e Khrakovsky DA, Tao C, Johnson ML, Thornbury RT, Shevick SL, Toste FD. Angew. Chem. Int. Ed. 2016; 55: 6079
    • 5f Miaskiewicz A, Weibel J.-M, Pale P, Blanc A. Org. Lett. 2016; 18: 844
    • 5g Shu C, Wang Y.-H, Shen C.-H, Ruan P.-P, Lu X, Ye L.-W. Org. Lett. 2016; 18: 3254
    • 5h Wang B, Liang M, Tang J, Deng Y, Zhao J, Sun H, Tung C.-H, Jia J, Xu Z. Org. Lett. 2016; 18: 4614
    • 5i Shu C, Shen C.-H, Wang Y.-H, Li L, Li T, Lu X, Ye L.-W. Org. Lett. 2016; 18: 4630
    • 5j Yu Y.-F, Shu C, Tan T.-D, Li L, Rafique S, Ye L.-W. Org. Lett. 2016; 18: 5178
    • 5k Yu Z, Qiu H, Liu L, Zhang J. Chem. Commun. 2016; 52: 2257
    • 5l Cao Z.-Y, Zhao Y.-L, Zhou J. Chem. Commun. 2016; 52: 2537
    • 5m Zhao Y.-L, Cao Z.-Y, Zeng X.-P, Shi J.-M, Yu Y.-H, Zhou J. Chem. Commun. 2016; 52: 3643
    • 5n Ma B, Wu Z, Huang B, Liu L, Zhang J. Chem. Commun. 2016; 52: 9351
    • 5o Kothandaraman P, Zhao Y, Lee BR, Le Ng CJ, Lee JY, Ayers BJ, Chan PW. H. Adv. Synth. Catal. 2016; 358: 1385
    • 5p Singh RR, Liu R.-S. Adv. Synth. Catal. 2016; 358: 1421
    • 5q Carrër A, Pean C, Perron-Sierra F, Mirguet O, Michelet V. Adv. Synth. Catal. 2016; 358: 1540
    • 6a Zhang G, Peng Y, Cui L, Zhang L. Angew. Chem. Int. Ed. 2009; 48: 3112
    • 6b Zhang G, Cui L, Wang Y, Zhang L. J. Am. Chem. Soc. 2010; 132: 1474
    • 6c Brenzovich WE, Benitez D, Lackner AD, Shunatona HP, Tkatchouk E, Goddard WA, Toste FD. Angew. Chem. Int. Ed. 2010; 49: 5519
    • 6d Melhado AD, Brenzovich WE, Lackner AD, Toste FD. J. Am. Chem. Soc. 2010; 132: 8885
    • 6e Mankad NP, Toste FD. J. Am. Chem. Soc. 2010; 132: 12859
    • 6f Hopkinson MN, Tessier A, Salisbury A, Giuffedi GT, Combettes LE, Gee AD, Gouverneur V. Chem. Eur. J. 2010; 16: 4739
    • 6g Brenzovich WE, Brazeau JF, Toste FD. Org. Lett. 2010; 12: 4728
    • 6h Ball LT, Green M, Lloyd-Jones GC, Russell CA. Org. Lett. 2010; 12: 4724
    • 6i Hopkinson MN, Ross JE, Giuffredi GT, Gee AD, Gouverneur V. Org. Lett. 2010; 12: 4904
    • 6j Wang W, Jasinski J, Hammond GB, Xu B. Angew. Chem. Int. Ed. 2010; 49: 7247
    • 6k de Haro T, Nevado C. Angew. Chem. Int. Ed. 2011; 50: 906
    • 6l Zhang G, Luo Y, Wang Y, Zhang L. Angew. Chem. Int. Ed. 2011; 50: 4450
    • 6m Leyva-Pérez A, Doménech A, Al-Resayes SI, Corma A. ACS Catal. 2012; 2: 121
    • 6n Arcadi A, Pietropaolo E, Alvino A, Michelet V. Org. Lett. 2013; 15: 2766
    • 6o Zhang R, Xu Q, Chen K, Gu P, Shi M. Eur. J. Org. Chem. 2013; 7366
    • 6p Shu C, Li L, Shen C.-H, Ruan P.-P, Liu C.-Y, Ye L.-W. Chem. Eur. J. 2016; 22: 2282
  • 7 Zhang Q, Zhang Z.-Q, Fu Y, Yu H.-Z. ACS Catal. 2016; 6: 798
  • 8 Huang L, Rominger F, Rudolph M, Hashmi AS. K. Chem. Commun. 2016; 52: 6435
  • 9 Sahoo B, Hopkinson MN, Glorius F. J. Am. Chem. Soc. 2013; 135: 5505
  • 10 Hopkinson MN, Sahoo B, Glorius F. Adv. Synth. Catal. 2014; 356: 2794
  • 11 Xia Z, Khaled O, Mouriès-Mansuy V, Ollivier C, Fensterbank L. J. Org. Chem. 2016; 81: 7182
  • 12 Shu X.-Z, Zhang M, He Y, Frei H, Toste FD. J. Am. Chem. Soc. 2014; 136: 5844
  • 13 Um J, Yun H, Shin S. Org. Lett. 2016; 18: 484
  • 14 Tlahuext-Aca A, Hopkinson MN, Garza-Sanchez RA, Glorius F. Chem. Eur. J. 2016; 22: 5909
  • 15 Alcaide B, Almendros P, Busto E, Luna A. Adv. Synth. Catal. 2016; 358: 1526
  • 16 He Y, Wu H, Toste FD. Chem. Sci. 2015; 6: 1194
  • 17 Tlahuext-Aca A, Hopkinson MN, Sahoo B, Glorius F. Chem. Sci. 2016; 7: 89
  • 18 Kim S, Rojas-Martin J, Toste FD. Chem. Sci. 2016; 7: 85
  • 19 Cornilleau T, Hermange P, Fouquet E. Chem. Commun. 2016; 52: 10040
  • 20 Gauchot V, Lee A.-L. Chem. Commun. 2016; 52: 10163
  • 21 During the preparation of this manuscript, an excellent relevant review was published, see: Hopkinson MN, Tlahuext-Aca A, Glorius F. Acc. Chem. Res. 2016; 49: 2261