Thieme Chemistry Journals Awardees – Where Are They Now?What’s Golden: Recent Advances in Organic Transformations Using Photoredox Gold Catalysis

Terry McCallum; Samantha Rohe; Louis Barriault

doi:10.1055/s-0036-1588644

Synlett, Inhaltsverzeichnis

Synlett 2017; 28(03): 289-305
DOI: 10.1055/s-0036-1588644

account

Thieme Chemistry Journals Awardees – Where Are They Now?
What’s Golden: Recent Advances in Organic Transformations Using Photoredox Gold Catalysis

Terry McCallum

Centre for Catalysis, Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa, 10 Marie Curie, Ottawa, Ontario, K1N 6N5, Canada eMail: Louis.Barriault@uottawa.ca

,

Samantha Rohe

Centre for Catalysis, Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa, 10 Marie Curie, Ottawa, Ontario, K1N 6N5, Canada eMail: Louis.Barriault@uottawa.ca

,

Louis Barriault*

Centre for Catalysis, Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa, 10 Marie Curie, Ottawa, Ontario, K1N 6N5, Canada eMail: Louis.Barriault@uottawa.ca

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

Light-mediated photoredox transformations have become commonplace in contemporary catalysis research and design. Excited-state redox catalysts trigger photoinduced electron transfers (PET) through oxidative or reductive quenching modes, allowing access to one-electron variations of classic radical reactions and the discovery of new transformations in organic chemistry. Herein, the use of Au-based photoredox catalysts containing powerful redox properties along with the emergence of dual catalyzed organic transformations involving photoredox catalysis and Au complexes for the Au(I)/Au(III) redox couple without use of stoichiometric oxidants will be discussed.

1 Principles of Photochemistry and Gold

2 Photoredox Transformations with Dimeric Gold Complexes

3 Dual Catalysis Involving Au(I)/Au(III) Redox Cycles

4 Concluding Remarks

Key words

photoredox catalysis - gold - photochemistry - heterocycles - organic transformations - Au(I)/Au(III) catalyzed couplings

Volltext

Referenzen

References
1 Hashmi AS. K. Chem. Rev. 2007; 107: 3180

2a Hopkinson MN, Gee AD, Gouverneur V. Chem. Eur. J. 2011; 17: 8248
2b Wegner HA, Auzias M. Angew. Chem. Int. Ed. 2011; 50: 8236
2c Zheng Z, Wang Z, Wang Y, Zhang L. Chem. Soc. Rev. 2016; 45: 4448

For seminal description, characterization and theoretical studies of aurophilic interactions in polynuclear Au(I) complexes:

3a Schmidbaur H, Wohlleben A, Schubert U, Frank A, Huttner G. Chem. Ber. 1977; 110: 2751
3b Briant OE, Hall KP, Mingos DM. P. J. Organomet. Chem. 1982; 229: C5
3c Shain J, Fackler JrJ. P. Inorg. Chim. Acta 1987; 131: 157
3d Payne NC, Puddephatt RJ, Ravindranath R, Treurnicht I. Can. J. Chem. 1988; 66: 3176
3e Che C.-M, Kwong H.-L, Yam VW.-W, Cho K.-C. J. Chem. Soc., Chem. Commun. 1989; 885
3f Jaw HR. C, Savas MM, Mason WR. Inorg. Chem. 1989; 28: 4366
3g Jaw HR. C, Savas MM, Rogers RD, Mason WR. Inorg. Chem. 1989; 28: 1028
3h King C, Wang JC, Khan MN. I, Fackler JP. Inorg. Chem. 1989; 28: 2145
3i Che C.-M, Kwong H.-L, Poon C.-K, Yam VW.-W. J. Chem. Soc., Dalton Trans. 1990; 3215
3j Yam VW.-W, Lai T.-F, Che C.-M. J. Chem. Soc., Dalton Trans. 1990; 3747
3k Pyykkö P, Zhao Y. Angew. Chem., Int. Ed. Engl. 1991; 30: 604
3l Che C.-M, Yip H.-K, Yam VW.-W, Cheung P.-Y, Lai T.-F, Shieh S.-J, Peng S.-M. J. Chem. Soc., Dalton Trans. 1992; 427
3m King C, Khan MN. I, Staples RJ, Fackler JP. Inorg. Chem. 1992; 31: 3236
3n Li D, Che C.-M, Kwong H.-L, Yam VW.-W. J. Chem. Soc., Dalton Trans. 1992; 3325
3o Forward JM, Assefa Z, Fackler JP. J. Am. Chem. Soc. 1995; 117: 9103
3p Pyykkö P, Mendizabal F. Inorg. Chem. 1998; 37: 3018
3q Fu W.-F, Chan K.-C, Miskowski VM, Che C.-M. Angew. Chem. Int. Ed. 1999; 38: 2783
3r Leung KH, Phillips DL, Tse M.-C, Che C.-M, Miskowski VM. J. Am. Chem. Soc. 1999; 121: 4799
3s Brandys M.-C, Jennings MC, Puddephatt RJ. J Chem. Soc., Dalton Trans. 2000; 4601
3t Fu W.-F, Chan K.-C, Cheung K.-K, Che C.-M. Chem. Eur. J. 2001; 7: 4656
3u Rawashdeh-Omary MA, Omary MA, Patterson HH, Fackler JP. J. Am. Chem. Soc. 2001; 123: 11237
3v Zhang H.-X, Che C.-M. Chem. Eur. J. 2001; 7: 4887
3w Leung KH, Phillips DL, Mao Z, Che C.-M, Miskowski VM, Chan C.-K. Inorg. Chem. 2002; 41: 2054
3x Barnard PJ, Baker MV, Berners-Price SJ, Skelton BW, White AH. Dalton Trans. 2004; 1038
3y Pan Q.-J, Zhang H.-X. J. Phys. Chem. A 2004; 108: 3650
3z Che C.-M, Lai S.-W. Coord. Chem. Rev. 2005; 249: 1296
3aa Mendizabal F, Olea-Azar C. Int. J. Quantum Chem. 2005; 103: 34
3ab Mendizabal F, Olea-Azar C, Briones R. J. Mol. Struct. (Theochem) 2006; 764: 187
3ac Yam VW. W, Chung-Chin Cheng E In Topics in Current Chemistry . Vol. 281. Balzani V, Campagna S. Springer; Berlin Heidelberg: 2007
3ad Tong GS. M, Kui SC. F, Chao H.-Y, Zhu N, Che C.-M. Chem. Eur. J. 2009; 15: 10777
3ae Cui G, Cao X.-Y, Fang W.-H, Dolg M, Thiel W. Angew. Chem. Int. Ed. 2013; 52: 10281
3af Seki T, Sakurada K, Muromoto M, Ito H. Chem. Sci. 2015; 6: 1491

4 Ma Y, Che C.-M, Chao H.-Y, Zhou X, Chan W.-H, Shen J. Adv. Mater. 1999; 11: 852
5 Zou T, Lum CT, Lok C.-N, To W.-P, Low K.-H, Che C.-M. Angew. Chem. Int. Ed. 2014; 53: 5810

6a Principles of Molecular Photochemistry: An Introduction . Turro NJ, Scaiano JC, Ramamurthy V. University Science Books; Sausalito: 2009
6b Roundhill DM In Photochemistry and Photophysics of Metal Complexes . Fackler JP. Jr. Springer; New York: 1994

7 Ma C, Chan CT.-L, To W.-P, Kwok W.-M, Che C.-M. Chem. Eur. J. 2015; 21: 13888
8 McTiernan CD, Morin M, McCallum T, Scaiano JC, Barriault L. Catal. Sci. Technol. 2016; 6: 201

9a Ciamician G. Science 1912; 36: 385
9b Balzani V, Credi A, Venturi M. ChemSusChem 2008; 1: 26

10a Prier CK, Rankic DA, MacMillan DW. C. Chem. Rev. 2013; 113: 5322
10b Hopkinson MN, Sahoo B, Li J.-L, Glorius F. Chem. Eur. J. 2014; 20: 3874
10c Pitre SP, McTiernan CD, Scaiano JC. Acc. Chem. Res. 2016; 49: 1320
10d Pitre SP, McTiernan CD, Scaiano JC. ACS Omega 2016; 1: 66
10e Romero NA, Nicewicz DA. Chem. Rev. 2016; 116: 10075
10f Bengough WI, McIntosh SA, Thomson RA. M. Nature 1959; 184: 266
10g Kuhn HJ, Braslavsky SE, Schmidt R. Pure Appl. Chem. 2004; 76: 2105
10h Ismaili H, Pitre SP, Scaiano JC. Catal. Sci. Technol. 2013; 3: 935
10i Majek M, Filace F, Jacobi von Wangelin A. Beilstein J. Org. Chem. 2014; 10: 981
10j Pitre SP, Mctiernan CD, Vine W, DiPucchio R, Grenier M, Scaiano JC. Sci. Rep. 2015; 5: 16397
10k Cismesia MA, Yoon TP. Chem. Sci. 2015; 6: 5426

11a Radicals in Organic Synthesis . Renaud P, Sibi MP. Wiley-VCH; Weinheim: 2001
11b Encyclopedia of Radicals in Chemistry, Biology and Materials . Vols. 1 and 2. Chatgilialoglu C, Studer A. Wiley; Chichester: 2012

12a Fry AJ, Krieger RL. J. Org. Chem. 1976; 41: 54
12b Rondinini S, Mussini PR, Muttini P, Sello G. Electrochim. Acta 2001; 46: 3245
12c Roth HG, Romero NA, Nicewicz DA. Synlett 2016; 27: 714

13 Revol G, McCallum T, Morin M, Gagosz F, Barriault L. Angew. Chem. Int. Ed. 2013; 52: 13342
14 McCallum T, Slavko E, Morin M, Barriault L. Eur. J. Org. Chem. 2015; 81
15 Kaldas SJ, Cannillo A, McCallum T, Barriault L. Org. Lett. 2015; 17: 2864

16a McCallum T, Barriault L. Chem. Sci. 2016; 7: 4754

For seminal work:

16b Minisci F, Bernardi R, Bertini F, Galli R, Perchinummo M. Tetrahedron 1971; 27: 3575

17 Xie J, Li J, Weingand V, Rudolph M, Hashmi AS. K. Chem. Eur. J. 2016; 22: 12646
18 Cannillo A, Schwantje TR, Bégin M, Barabé F, Barriault L. Org. Lett. 2016; 18: 2592
19 Nzulu F, Telitel S, Stoffelbach F, Graff B, Morlet-Savary F, Lalevee J, Fensterbank L, Goddard J.-P, Ollivier C. Polym. Chem. 2015; 6: 4605
20 Xie J, Zhang T, Chen F, Mehrkens N, Rominger F, Rudolph M, Hashmi AS. K. Angew. Chem. Int. Ed. 2016; 55: 2934
21 Xie J, Shi S, Zhang T, Mehrkens N, Rudolph M, Hashmi AS. K. Angew. Chem. Int. Ed. 2015; 54: 6046
22 Tran H, McCallum T, Morin M, Barriault L. Org. Lett. 2016; 18: 4308
23 Zhang Q, Zhang Z.-Q, Fu Y, Yu H.-Z. ACS Catal. 2016; 6: 798

24a Huang L, Rominger F, Rudolph M, Hashmi AS. K. Chem. Commun. 2016; 52: 6435
24b Huang L, Rudolph M, Rominger F, Hashmi AS. K. Angew. Chem. Int. Ed. 2016; 55: 4808

25 Tlahuext-Aca A, Hopkinson MN, Daniliuc CG, Glorius F. Chem. Eur. J. 2016; 22: 11587
26 Sahoo B, Hopkinson MN, Glorius F. J. Am. Chem. Soc. 2013; 135: 5505

27a Hopkinson MN, Sahoo B, Glorius F. Adv. Synth. Catal. 2014; 356: 2794

For β-hydride elimination processes with Au-based complexes:

27b Rekhroukh F, Estevez L, Mallet-Ladeira S, Miqueu K, Amgoune A, Bourissou D. J. Am. Chem. Soc. 2016; 138: 11920
27c Rei MC, Lopez CS, Kraka E, Cremer D, Faza ON. Inorg. Chem. 2016; 55: 8636

28 Shu X.-z, Zhang M, He Y, Frei H, Toste FD. J. Am. Chem. Soc. 2014; 136: 5844
29 He Y, Wu H, Toste FD. Chem. Sci. 2015; 6: 1194
30 Um J, Yun H, Shin S. Org. Lett. 2016; 18: 484
31 Tlahuext-Aca A, Hopkinson MN, Garza-Sanchez RA, Glorius F. Chem. Eur. J. 2016; 22: 5909
32 Alcaide B, Almendros P, Busto E, Luna A. Adv. Synth. Catal. 2016; 358: 1526
33 Xia Z, Khaled O, Mouriès-Mansuy V, Ollivier C, Fensterbank L. J. Org. Chem. 2016; 81: 7182
34 Cai R, Lu M, Aguilera EY, Xi Y, Akhmedov NG, Petersen JL, Chen H, Shi X. Angew. Chem. Int. Ed. 2015; 54: 8772
35 Peng H, Cai R, Xu C, Chen H, Shi X. Chem. Sci. 2016; 7: 6190
36 Tlahuext-Aca A, Hopkinson MN, Sahoo B, Glorius F. Chem. Sci. 2016; 7: 89
37 Kim S, Rojas-Martin J, Toste FD. Chem. Sci. 2016; 7: 85

38a Cornilleau T, Hermange P, Fouquet E. Chem. Commun. 2016; 52: 10040
38b Gauchot V, Lee A.-L. Chem. Commun. 2016; 52: 10163

39 Patil DV, Yun H, Shin S. Adv. Synth. Catal. 2015; 357: 2622
40 During the review process of this account another account on dual gold photoredox catalysis appeared: Hopkinson MH, Tlahuext-Aca A, Glorius F. Acc. Chem. Res. 2016; 2261