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Synlett 2023; 34(07): 698-708
DOI: 10.1055/a-1893-7653
DOI: 10.1055/a-1893-7653
account
Chemical Synthesis and Catalysis in India
Gold-Catalyzed Cross-Coupling and 1,2-Difunctionalization Reactions: A Personal Account
Generous financial support by the Science and Engineering Research Board (SERB), New Delhi (File No. DIA/2018/000016) is gratefully acknowledged.
Abstract
In recent years, gold catalysis involving Au(I)/Au(III) redox cycle has gained significant attention. This account summarizes our contributions to the development of Au(I)/Au(III) catalysis, focusing on cross-coupling reactions and 1,2-difunctionalization reactions of C–C multiple bonds. A special emphasis has been given to understanding the mechanism of the reactions.
1 Introduction
2 Gold-Catalyzed Cross-Coupling Reactions
3 Gold-Catalyzed 1,2-Difunctionalization of C–C Multiple Bonds
4 Conclusion and Outlook
Publication History
Received: 31 May 2022
Accepted after revision: 07 July 2022
Accepted Manuscript online:
07 July 2022
Article published online:
09 August 2022
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References
- 1a Catalysis by Gold . Bond GC, Louis C, Thompson DT. Imperial College Press; London: 2006
- 1b Modern Gold Catalyzed Synthesis . Hashmi AS. K, Toste FD. Wiley-VCH; Weinheim: 2012
- 1c Gold Catalysis: An Homogeneous Approach . Toste FD, Michelet V. Imperial College Press; London: 2014
- 1d Gold Catalysis: Preparation, Characterization, and Applications . Prati L, Villa A. Pan Stanford Publishing; Singapore: 2015
- 1e Homogeneous Gold Catalysis . In Topics in Current Chemistry . Slaughter LM, Aponick A. Springer; Cham: 2015
- 2a Li Z, Brouwer C, He C. Chem. Rev. 2008; 108: 3239
- 2b Arcadi A. Chem. Rev. 2008; 108: 3266
- 2c Jiémnez-Núñez E, Echavarren AM. Chem. Rev. 2008; 108: 3326
- 2d Gorin DJ, Sherry BD, Toste FD. Chem. Rev. 2008; 108: 3351
- 2e Patil NT, Yamamoto Y. Chem. Rev. 2008; 108: 3395
- 2f Hashmi AS. K, Rudolph M. Chem. Soc. Rev. 2008; 37: 1766
- 2g Hashmi AS. K. Angew. Chem. Int. Ed. 2010; 49: 5232
- 2h Corma A, Leyva-Pérez A, Sabater MJ. Chem. Rev. 2011; 111: 1657
- 2i Krause N, Winter C. Chem. Rev. 2011; 111: 1994
- 2j Bandini M. Chem. Soc. Rev. 2011; 40: 1358
- 2k Boorman TC, Larrosa I. Chem. Soc. Rev. 2011; 40: 1910
- 2l Rudolph M, Hashmi AS. K. Chem. Commun. 2011; 47: 6536
- 2m Rudolph M, Hashmi AS. K. Chem. Soc. Rev. 2012; 41: 2448
- 2n Lu B.-L, Dai L, Shi M. Chem. Soc. Rev. 2012; 41: 3318
- 2o Brenzovich WE. Jr. Angew. Chem. Int. Ed. 2012; 51: 8933
- 2p Garayalde D, Nevado C. ACS Catal. 2012; 2: 1462
- 2q Patil NT. Curr. Sci. 2013; 104: 1671
- 2r Braun I, Asiri AM, Hashmi AS. K. ACS Catal. 2013; 3: 1902
- 2s Hashmi AS. K. Acc. Chem. Res. 2014; 47: 864
- 2t Zhang L. Acc. Chem. Res. 2014; 47: 877
- 2u Obradors C, Echavarren AM. Acc. Chem. Res. 2014; 47: 902
- 2v Zhang D.-H, Tang X.-Y, Shi M. Acc. Chem. Res. 2014; 47: 913
- 2w Fensterbank L, Malacria M. Acc. Chem. Res. 2014; 47: 953
- 2x Zhang Y, Luo T, Yang Z. Nat. Prod. Rep. 2014; 31: 489
- 2y Cañeque T, Truscott FM, Rodriguez R, Maestriab G, Malacria M. Chem. Soc. Rev. 2014; 43: 2916
- 2z Yang W, Hashmi AS. K. Chem. Soc. Rev. 2014; 43: 2941
- 2aa Muratore ME, Homs A, Obradors C, Echavarren AM. Chem. Asian J. 2014; 9: 3066
- 2ab Dorel R, Echavarren AM. Chem. Rev. 2015; 115: 9028
- 2ac Inamdar SM, Patil NT. Org. Chem. Front. 2015; 2: 995
- 2ad Jia M, Bandini M. ACS Catal. 2015; 5: 1638
- 2ae Ranieri B, Escofet I, Echavarren AM. Org. Biomol. Chem. 2015; 13: 7103
- 2af Qiana D, Zhang J. Chem. Soc. Rev. 2015; 44: 677
- 2ag Goodwina JA, Aponick A. Chem. Commun. 2015; 51: 8730
- 2ah Liu L, Zhang J. Chem. Soc. Rev. 2016; 45: 506
- 2ai Asiria AM, Hashmi AS. K. Chem. Soc. Rev. 2016; 45: 4471
- 2aj Bansode AH, Chimala P, Patil NT. ChemCatChem 2017; 9: 30
- 2ak Sugimoto K, Matsuya Y. Tetrahedron Lett. 2017; 58: 4420
- 2al Chintawar CC, Yadav AK, Kumar A, Sancheti SP, Patil NT. Chem. Rev. 2021; 121: 8478
- 2am Witzel S, Hashmi SK, Xie J. Chem. Rev. 2021; 121: 8868
- 2an Wang W, Ji C.-L, Liu K, Zhao C.-G, Li W, Xie J. Chem. Soc. Rev. 2021; 50: 1874
- 2ao Kumar A, Patil NT. ACS Sustainable Chem. Eng. 2022; 10: 6900
- 3 Bratsch SG. J. Phys. Chem. Ref. Data 1989; 18: 1
- 4a Bhoyare VW, Tathe AG, Das A, Chintawar CC, Patil NT. Chem. Soc. Rev. 2021; 50: 10422
- 4b Huang B, Hu M, Toste FD. Trends Chem. 2020; 2: 707
- 4c Akram MO, Banerjee S, Saswade SS, Bedi V, Patil NT. Chem. Commun. 2018; 54: 11069
- 4d Font P, Ribas X. Eur. J. Inorg. Chem. 2021; 2556
- 5a Zhang G, Peng Y, Cui L, Zhang L. Angew. Chem. Int. Ed. 2009; 48: 3112
- 5b Melhado AD, Brenzovich WE. Jr, Lackner AD, Toste FD. J. Am. Chem. Soc. 2010; 132: 8885 For reviews, see
- 5c Garcia P, Malacria M, Aubert C, Gandon V, Fensterbank L. ChemCatChem 2010; 2: 493
- 5d Wegner HA, Auzias M. Angew. Chem. Int. Ed. 2011; 50: 8236
- 5e Hopkinson MN, Gee AD, Gouverneur V. Chem. Eur. J. 2011; 17: 8248
- 5f Miro J, del Pozo C. Chem. Rev. 2016; 116: 11924
- 5g Nijamudheen A, Datta A. Chem. Eur. J. 2020; 26: 1442
- 5h Zheng Z, Ma X, Cheng X, Zhao K, Gutman K, Li T, Zhang L. Chem. Rev. 2021; 121: 8979
- 6a Sahoo B, Hopkinson MN, Glorius F. J. Am. Chem. Soc. 2013; 135: 5505 For reviews, see
- 6b Hopkinson MN, Tlahuext-Aca A, Glorius F. Acc. Chem. Res. 2016; 49: 2261
- 6c Akram MO, Banerjee S, Saswade SS, Bedi V, Patil NT. Chem. Commun. 2018; 54: 11069
- 6d Witzel S, Hashmi AS. K, Xie J. Chem. Rev. 2021; 121: 8868
- 6e Font P, Ribas X. Eur. J. Inorg. Chem. 2021; 2556
- 7a Garcia P, Malacria M, Aubert C, Gandon V, Fensterbank L. ChemCatChem 2010; 2: 493
- 7b Wegner HA, Auzias M. Angew. Chem. Int. Ed. 2011; 50: 8236
- 7c Hopkinson MN, Gee AD, Gouverneur V. Chem. Eur. J. 2011; 17: 8248
- 7d Miró J, del Pozo C. Chem. Rev. 2016; 116: 11924
- 7e Nijamudheen A, Datta A. Chem. Eur. J. 2020; 26: 1442
- 7f Kramer S. Synthesis 2020; 2017
- 7g Banerjee S, Bhoyare VW, Patil NT. Chem. Commun. 2020; 56: 2677
- 8a Zeineddine A, Estévez L, Mallet-Ladeira S, Miqueu K, Amgoune A, Bourissou D. Nat. Commun. 2017; 8: 565
- 8b Messina MS, Stauber JM, Waddington MA, Rheingold AL, Maynard HD, Spokoyny AM. J. Am. Chem. Soc. 2018; 140: 7065
- 8c Rodriguez J, Zeineddine A, Sosa Carrizo ED, Miqueu K, Saffon-Merceron N, Amgoune A, Bourissou D. Chem. Sci. 2019; 10: 7183
- 8d Akram MO, Das A, Chakrabarty I, Patil NT. Org. Lett. 2019; 21: 8101
- 8e Rodriguez J, Adet N, Saffon-Merceron N, Bourissou D. Chem. Commun. 2020; 56: 94
- 8f Stauber JM, Qian EA, Han Y, Rheingold AL, Král P, Fujita D, Spokoyny AM. J. Am. Chem. Soc. 2020; 142: 327
- 8g Stauber JM, Rheingold AL, Spokoyny AM. Inorg. Chem. 2021; 60: 5054
- 8h Rodriguez J, Vesseur D, Tabey A, Mallet-Ladeira S, Miqueu K, Bourissou D. ACS Catal. 2022; 12: 993
- 9a Shaikh AC, Shinde DR, Patil NT. Org. Lett. 2016; 18: 1056
- 9b Akram MO, Bera S, Patil NT. Chem. Commun. 2016; 52: 12306
- 9c Bagle PN, Mane MV, Vanka K, Shinde DR, Shaikh SR, Gonnade RG, Patil NT. Chem. Commun. 2016; 52: 14462
- 9d Gade AB, Patil NT. Org. Lett. 2016; 18: 1844
- 9e Inamdar SM, Gonnade RG, Patil NT. Org. Biomol. Chem. 2017; 15: 863
- 9f Chakrabarty I, Inamdar SM, Akram MO, Gade AB, Banerjee S, Bera S, Patil NT. Chem. Commun. 2017; 53: 196
- 9g Sancheti SP, Akram MO, Roy R, Bedi V, Kundu S, Patil NT. Chem. Asian J. 2019; 14: 4601
- 9h Bagle PN, Mane MV, Sancheti SP, Gade AB, Shaikh SR, Baik M.-H, Patil NT. Org. Lett. 2019; 21: 335
- 10a Li X, Xin X, Sun N, Liu Y. Angew. Chem. Int. Ed. 2017; 56: 6994
- 10b Banerjee S, Patil NT. Chem. Commun. 2017; 53: 7937
- 11 Peng H, Xi Y, Ronaghi N, Dong B, Akhmedov NG, Shi X. J. Am. Chem. Soc. 2014; 136: 13174
- 12 Sahoo B, Hopkinson MN, Glorius F. J. Am. Chem. Soc. 2013; 135: 5505
- 13a Inamdar SM, Shinde VS, Patil NT. Org. Biomol. Chem. 2015; 13: 8116
- 13b Inamdar SM, Konala A, Patil NT. Chem. Commun. 2014; 50: 15124
- 14 Akram MO, Banerjee S, Saswade SS, Bedi V, Patil NT. Chem. Commun. 2018; 54: 11069
- 15 Akram MO, Shinde PS, Chintawar CC, Patil NT. Org. Biomol. Chem. 2018; 16: 2865
- 16 Sancheti SP, Urvashi Urvashi, Shah MP, Patil NT. ACS Catal. 2020; 10: 3462
- 17 Chakrabarty I, Akram MO, Biswas S, Patil NT. Chem. Commun. 2018; 54: 7223
- 18 Akram MO, Mali PS, Patil NT. Org. Lett. 2017; 19: 3075
- 19 Akram MO, Das A, Chakrabarty I, Patil NT. Org. Lett. 2019; 21: 8101
- 20 Rodriguez J, Adet N, Saffon-Merceron N, Bourissou D. Chem. Commun. 2020; 56: 94
- 21 Tathe, A. G.; Patil, N. T. Org. Lett., 2022, 24, 4459.
- 22 Bansode AH, Shaikh SR, Gonnade RG, Patil NT. Chem. Commun. 2017; 53: 9081
- 23 Shinde PS, Shaikh AC, Patil NT. Chem. Commun. 2016; 52: 8152
- 24a Paroi B, Sancheti S, Patil NT. Chem. Rev. 2021; 21: 3779 Representative reports
- 24b Mule RD, Shaikh AC, Gade AB, Patil NT. Chem. Commun. 2018; 54: 11909
- 24c Shaikh AC, Banerjee S, Mule RD, Bera S, Patil NT. J. Org. Chem. 2019; 84: 4120
- 24d Shaikh AC, Varma ME, Mule RD, Banerjee S, Kulkarni PP, Patil NT. J. Org. Chem. 2019; 84: 1766
- 24e Shaikh AC, Ranade DS, Thorat S, Maity A, Kulkarni PP, Gonnade RG, Munshi P, Patil NT. Chem. Commun. 2015; 51: 16115
- 24f Shaikh AC, Shalini S, Vaidhyanathan R, Mane MV, Barui AK, Patra CR, Venkatesh Y, Bangal PR, Patil NT. Eur. J. Org. Chem. 2015; 22: 4860
- 25 Shaikh AC, Ranade DS, Rajamohanan PR, Kulkarni PP, Patil NT. Angew. Chem. Int. Ed. 2017; 56: 757
- 26 Shaikh AC, Varma ME, Mule RD, Banerjee S, Kulkarni PP, Patil NT. J. Org. Chem. 2019; 84: 1766
- 27 Banerjee S, Ambegave SB, Mule RD, Senthilkumar B, Patil NT. Org. Lett. 2020; 22: 4792
- 28 Hari Babu M, Dwivedi V, Kant R, Sridhar Reddy M. Angew. Chem. Int. Ed. 2015; 54: 3783
- 29 Chintawar CC, Yadav AK, Patil NT. Angew. Chem. Int. Ed. 2020; 59: 11808
- 30a Saini V, Sigman MS. J. Am. Chem. Soc. 2012; 134: 11372
- 30b McCammant MS, Liao L, Sigman MS. J. Am. Chem. Soc. 2013; 135: 4167
- 30c Liu Z, Zeng T, Yang KS, Engle KM. J. Am. Chem. Soc. 2016; 138: 15122
- 30d Shrestha B, Basnet P, Dhungana RK, Shekhar KC, Thapa S, Sears JM, Giri R. J. Am. Chem. Soc. 2017; 139: 10653
- 30e Derosa J, Tran VT, Boulous MN, Chen JS, Engle KM. J. Am. Chem. Soc. 2017; 139: 10657
- 30f Thapa S, Dhungana RK, Magar RT, Shrestha B, KC S, Giri R. Chem. Sci. 2018; 9: 904
- 30g You W, Brown MK. J. Am. Chem. Soc. 2014; 136: 14730
- 30h Thapa S, Basnet P, Giri R. J. Am. Chem. Soc. 2017; 139: 5700
- 31 Tathe AG, Chintawar CC, Bhoyare VW, Patil NT. Chem. Commun. 2020; 56: 9304
- 32 Rigoulet M, du Boullay OT, Amgoune A, Bourissou D. Angew. Chem. Int. Ed. 2020; 59: 16625
- 33 Zhang S, Wang C, Ye X, Shi X. Angew. Chem. Int. Ed. 2020; 59: 20470
- 34 Tathe AG, Urvashi Urvashi, Yadav AK, Chintawar CC, Patil NT. ACS Catal. 2021; 11: 4576
- 35 Chintawar CC, Bhoyare VW, Mane MV, Patil NT. J. Am. Chem. Soc. 2022; 144: 7089
- 36 Ye X, Wang C, Zhang S, Tang Q, Wojtas L, Li M, Shi X. Chem. Eur. J. 2022; e202201018
Books:
Selected reviews:
For selected reviews, see:
For seminal reports on external oxidant strategy, see:
For seminal reports on photoredox strategy, see:
Review: