CC BY-NC-ND 4.0 · SynOpen 2021; 05(02): 152-157
DOI: 10.1055/s-0040-1706048
paper

Visible-Light-Mediated Photocatalytic Oxidative C–C Bond Cleavage of Geminal Diazides: An Approach to Oxamates

a   Catalysis & Chemical Biology Laboratory, Department of Chemistry, Indian Institute of Technology (IIT) Hyderabad, Kandi, Sangareddy, Telangana 502 285, India
,
a   Catalysis & Chemical Biology Laboratory, Department of Chemistry, Indian Institute of Technology (IIT) Hyderabad, Kandi, Sangareddy, Telangana 502 285, India
,
Sonika Sharma
b   Loyola Academy Degree & P.G College, Old Alwal, Secunderabad, Telangana 500010, India
,
a   Catalysis & Chemical Biology Laboratory, Department of Chemistry, Indian Institute of Technology (IIT) Hyderabad, Kandi, Sangareddy, Telangana 502 285, India
› Author Affiliations
We gratefully acknowledge the Council of Scientific and Industrial Research (02(0297)/17/EMR-II), Government of India and the Indian Institute of Technology Hyderabad (IITH) for financial support. N.R.K. thanks the Indian Institute of Technology Hyderabad (IITH) and the Science and Engineering Research Board, Department of Science and Technology, Ministriy of Science and Technology, India (DST-SERB), and A.V.M thanks the University Grants Committee (UGC) for the award of research rellowships.


Dedicated to all covid-19 warriors

Abstract

Photoredox catalysis has received great attention in both academia and industry and remarkable progress has been made over the past decade. Now, it has been shown that a visible-light-mediated oxidative C–C bond cleavage of geminal diazides can be induced by organic dye catalysis for the synthesis of oxamates. A mechanistic study, confirmed by control experiments, indicates that this proceeds through single-electron transfer (SET). This methodology can be applied to convert a wide array of geminal diazides into oxamates.

Supporting Information



Publication History

Received: 05 May 2021

Accepted after revision: 18 May 2021

Publication Date:
17 June 2021 (online)

© 2021. This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

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  • References

  • 1 Sivaguru P, Wang Z, Zanoni G, Bi X. Chem. Soc. Rev. 2019; 48: 2615
  • 2 Adeli Y, Huang K, Liang Y, Jiang Y, Liu J, Song S, Zeng C.-C, Jiao N. ACS Catal. 2019; 9: 2063
    • 3a Long Z, Yang Y, You J. Org. Lett. 2017; 19: 2781
    • 3b Ni J, Jiang Y, An Z, Yan R. Org. Lett. 2018; 20: 1534
    • 3c Prakash R, Bora BR, Boruah RC, Gogoi S. Org. Lett. 2018; 20: 2297
    • 3d Onodera S, Ishikawa S, Kochi T, Kakiuchi F. J. Am. Chem. Soc. 2018; 140: 9788
  • 4 Tobisu M, Chatani N. Chem. Soc. Rev. 2008; 37: 300
  • 5 Moriarty RM, Penmasta R, Awasthi AK, Prakash I. J. Org. Chem. 1988; 53: 6124
    • 6a Shimada T, Yamamoto Y. J. Am. Chem. Soc. 2003; 125: 6646
    • 6b Datta S, Chang C.-L, Yeh K.-L, Liu R.-S. J. Am. Chem. Soc. 2003; 125: 9294
    • 6c Liu Y.-H, Songand F.-J, Guo S.-H. J. Am. Chem. Soc. 2006; 128: 11332
    • 6d Wang A.-Z, Jiang H.-F. J. Am. Chem. Soc. 2008; 130: 5030
    • 6e Liu Q.-L, Chen P.-H, Liu G.-S. ACS Catal. 2013; 3: 178
    • 6f Xie H.-Z, Gao Q, Liang Y, Wang H.-S, Pan Y.-M. Green Chem. 2014; 16: 2132
  • 7 Biallas P, Haring AP, Kirsch SF. Org. Biomol. Chem. 2017; 15: 3184
  • 8 Hypervalent Iodine Chemistry: Modern Developments in Organic Synthesis, Vol. 224. Wirth T. Springer; Berlin: 2003: 1-248
  • 9 Yu P, Wang Y, Zeng Z, Chen Y. J. Org. Chem. 2019; 84: 14883
  • 10 Yu T.-Y, Zheng Z.-J, Dang T.-T, Zhang F.-X, Wei H. J. Org. Chem. 2018; 83: 10589
    • 11a Marzo L, Pagire SK, Reiser O, König B. Angew. Chem. 2018; 130: 10188
    • 11b Pan Y, Kee CW, Chen L, Tan C.-H. Green Chem. 2011; 13: 2682
    • 11c Guo W.-L, Wang L.-Q, Wang Y.-N, Chen J.-R, Xiao W.-J. Angew. Chem. Int. Ed. 2015; 54: 2265 ; Angew. Chem. 2015, 127, 2293
    • 11d Wang L, Cheng P, Wang X, Wang W, Zeng J, Liang Y, Reiser O. Org. Chem. Front. 2019; 6: 3771
    • 11e Murugan A, Babu VN, Polu A, Sabarinathan N, Bakthadoss M, Sharada DS. J. Org. Chem. 2019; 84: 7796
  • 12 Sun H, Yang C, Gao F, Li Z, Xia W. Org. Lett. 2013; 15: 624
  • 13 Sharma S, Sharma A. Org. Biomol. Chem. 2019; 17: 4384
    • 14a Prier CK, Rankic DA, MacMillan DW. C. Chem. Rev. 2013; 113: 5322
    • 14b Reiser O. Eur. J. Org. Chem. 2019; 4973
    • 14c Arepally S, Chamuah A, Katta N, Sharada DS. Eur. J. Org. Chem. 2019; 7: 1542
    • 15a Dinsmore CJ, Beshore DC. Tetrahedron 2002; 58: 3297
    • 15b Dias LC, Ferreira MA. B. J. Org. Chem. 2012; 77: 4046
    • 15c Sellstedt JH, Guinosso CJ, Begany AJ, Bell SC, Rosenthale M. J. Med. Chem. 1975; 18: 926
    • 15d Wright JB, Hall CM, Johnson HG. N. J. Med. Chem. 1978; 21: 930
    • 15e Klaubert DH, Sellstedt JH, Guinosso CJ, Capetola RJ. Bell S. C. J. Med. Chem. 1981; 24: 742
    • 15f Gudipati NS, Palyam S, Vanjari SK, Challapalli S. Inorg. Chem. Commun. 2020; 119: 108112
    • 15g Gudipati NS, Palyam S, Vanjari SK, Challapalli S. Inorg. Chem. Commun. 2021; 129: 108627
    • 16a Palmer C, Morra NA, Stevens AC, Bajtos Machin BB. P, Pagenkopf BL. Org. Lett. 2009; 11: 5614
    • 16b Xu Y, McLaughlin M, Bolton EN, Reamer RA. J. Org. Chem. 2010; 75: 8666
    • 16c Lynn JW, English JJr. J. Am. Chem. Soc. 1951; 73: 4284
    • 16d Babu VN, Murugan A, Katta N, Sharada DS. J. Org. Chem. 2019; 84: 6631
    • 17a Zhang Z, Gao X, Yu H, Zhang G, Liu J. Adv. Synth. Catal. 2018; 360
    • 17b Adib M, Pashazadeh R, Gohari SJ. A. Synlett 2017; 28: 1481
    • 18a Arepally S, Babu VN, Polu A, Sharada DS. Eur. J. Org. Chem. 2018; 41: 5700
    • 18b Katta N, Murugan A, Ojha M, Arepally S. RSC Adv. 2020; 10: 12599
    • 19a Park S, Jeon WH, Yong W.-S, Lee PH. Org. Lett. 2015; 17: 5060
    • 19b Li J, Cai S, Chen J, Zhao Y, Wang DZ. Synlett 2014; 25: 1626