CC BY-ND-NC 4.0 · Synthesis 2019; 51(05): 1243-1252
DOI: 10.1055/s-0037-1611648
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Copyright with the author

Visible Light-Promoted Formation of C–B and C–S Bonds under Metal- and Photocatalyst-Free Conditions

Lena Blank
a  Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Email: magnus.rueping@rwth-aachen.de
,
Maurizio Fagnoni
b  PhotoGreen Lab, Department of Chemistry, University of Pavia, Viale Taramelli, 12, 27100 Pavia, Italy
,
Stefano Protti
b  PhotoGreen Lab, Department of Chemistry, University of Pavia, Viale Taramelli, 12, 27100 Pavia, Italy
,
a  Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Email: magnus.rueping@rwth-aachen.de
› Author Affiliations
Further Information

Publication History

Received: 30 November 2018

Accepted: 10 December 2018

Publication Date:
06 February 2019 (online)


Published as part of the 50 Years SYNTHESIS – Golden Anniversary Issue

Abstract

A green, efficient, photoinduced synthesis of arylboronic esters and aryl sulfides has been developed. Bench stable arylazo sulfones were used as radical precursors for a photocatalyst- and additive-free carbon–heteroatom bond formation under visible light. The protocols are applicable to a wide range of substrates, providing products in good yields.

Supporting Information

 
  • References

    • 1a Miyaura N, Suzuki A. Chem. Rev. 1995; 95: 2457
    • 1b Jana R, Pathak TP, Sigman MS. Chem. Rev. 2011; 111: 1417
    • 1c Yamaguchi J, Yamaguchi AD, Itami K. Angew. Chem. Int. Ed. 2012; 51: 8960
    • 1d Chauhan P, Mahajan S, Enders D. Chem. Rev. 2014; 114: 8807
    • 1e Xu L, Zhang S, Li P. Chem. Soc. Rev. 2015; 44: 8848
    • 1f Fang Y, Luo Z, Xu X. RSC Adv. 2016; 6: 59661
    • 1g Shen C, Zhang P, Sun Q, Bai S, Hor TS. A, Lui X. Chem. Soc. Rev. 2015; 44: 291
    • 2a Ishihara SO. K, Yamamoto H. J. Org. Chem. 1996; 61: 4196
    • 2b Antilla JC, Wulff WD. J. Am. Chem. Soc. 1999; 121: 5099
    • 2c Yamamoto H, Ishihara K, Maki T. Synlett 2004; 8: 1355
    • 2d Tang P. Org. Synth. 2005; 81: 262
    • 2e Stepanenko V, Ortiz-Marciales M, Correa W, Jesus MD, Espinosa S, Ortiz L. Tetrahedron: Asymmetry 2006; 17: 112
    • 2f Newman CA, Antilla JC, Chen P, Predeus AV, Fielding L, Wulff WD. J. Am. Chem. Soc. 2007; 121: 7216
    • 2g Mellah M, Voiturriez A, Schulz E. Chem. Rev. 2007; 107: 5133
  • 3 Brooks WL, Sumerlin BS. Chem. Rev. 2016; 116: 1375
    • 4a Alley MR, Baker SJ, Beutner KR, Plattner J. Expert Opin. Investig. Drugs 2007; 16: 157
    • 4b Hui X, Baker SJ, Wester RC, Barbadillo S, Cashmore AK, Sanders V, Hold KM, Akama T, Zhang YK, Plattner JJ, Maibach HI. J. Pharm. Sci. 2007; 96: 2622
    • 4c Vernon MW, Heel RC, Brogden RN. Drugs 1991; 42: 997
    • 4d Conlon DA, Drahus-Paone A, Ho GJ, Pipik B, Helmy R, McNamara JM, Shi YJ, Williams JM, Macdonald D, Deschenes D, Gallant M, Mastracchio A, Roy B, Scheigetz J. Org. Process Res. Dev. 2006; 10: 36
    • 4e Jarvest RL, Berge JM, Brown MJ, Brown P, Elder JS, Forrest AK, Houge-Frydrych CS. V, O’Hanlon PJ, McNair DJ, Rittenhouse S, Sheppard RJ. Bioorg. Med. Chem. Lett. 2003; 13: 665
    • 5a Waldrop FN, Robertson RH, Vourlekis A. Compr. Psychiatry 1961; 2: 96
    • 5b Brogden RN, Heel RC, Speight TM, Avery GS. Drugs 1978; 16: 97
    • 5c Schumacher DP, Clark JE, Murphy BL, Fischer PA. J. Org. Chem. 1990; 55: 5291
    • 5d Pallett KE, Little JP, Veerasekaran P, Viviani F. Pestic. Sci. 1997; 50: 83
    • 5e Lu WY, Chen P, Lin GQ. Tetrahedron 2008; 64: 7822
    • 5f Van Soolingen D, Hernandez-Pando R, Orozco H, Aguilar D, Magis-Escurra C, Amaral L, van Ingen J, Boeree MJ. PLoS One 2010; 5: e12640
    • 5g Dunbar L, Scharf DH, Litomska A, Hertweck C. Chem. Rev. 2017; 117: 5521
    • 6a Kane RC, Bross PF, Farrell AT, Padzur R. Oncologist 2003; 8: 508
    • 6b Feng M, Tang B, Liang SH, Jiang X. Curr. Top. Med. Chem. 2016; 16: 1200
    • 7a Trippler PC, McGuigan C. Med. Chem. Commun. 2010; 1: 183
    • 7b Ban HS, Nakamura H. Chem. Rec. 2015; 15: 616
    • 8a Brown HC, Cole TE. Organometallics 1983; 2: 1316
    • 8b Brown HC, Srebnik M, Cole TE. Organometallics 1986; 5: 2300
    • 8c Baron O, Knochel P. Angew. Chem. Int. Ed. 2005; 44: 3133
    • 9a Ishiyama T, Murata M, Miyaura N. J. Org. Chem. 1995; 60: 7508
    • 9b Chen H, Schlecht S, Semple TC, Hartwig JF. Science 2000; 287: 1995
    • 9c Shimada S, Batsanov AS, Howard JA. K, Marder TB. Angew. Chem. Int. Ed. 2001; 40: 2168
    • 9d Ishiyama T, Takagi J, Ishida K, Miyaura N, Anastasi NR, Hartwig JF. J. Am. Chem. Soc. 2002; 124: 390
    • 9e Ishiyama T, Miyaura N. J. Organomet. Chem. 2003; 680: 3
    • 9f Adams CJ, Baber RA, Batsanov AS, Bramham G, Charmant JP. H, Haddow MF, Howard JA. K, Lam WH, Lin Z, Marder TB, Norman NC, Orpen AG. Dalton Trans. 2006; 11: 1370
    • 9g Zhu W, Ma D. Org. Lett. 2006; 8: 261
    • 9h Billingsley KL, Barder TE, Buchwald SL. Angew. Chem. Int. Ed. 2007; 46: 5359
    • 9i Rosen BM, Huang C, Percec V. Org. Lett. 2008; 10: 2597
    • 9j Kleeberg C, Dang L, Lin Z, Marder TB. Angew. Chem. Int. Ed. 2009; 48: 5350
    • 9k Wilson DA, Wilson CJ, Moldoveanu C, Resmerita AM, Corcoran P, Hoang LM, Rosen BM, Percec V. J. Am. Chem. Soc. 2010; 132: 1800
    • 9l Mkhalid IA. I, Barnard JH, Marder TB, Murphy JM, Hartwig JF. Chem. Rev. 2010; 110: 890
    • 9m Moldoveanu C, Wilson DA, Wilson CJ, Leowanawat P, Resmerita A.-M, Liu C, Rosen BM, Percec V. J. Org. Chem. 2010; 75: 5438
    • 9n Chow WK, So CM, Lau CP, Kwong FY. Chem. Eur. J. 2011; 17: 6913
    • 9o Kawamorita S, Ohmiya H, Iwai T, Sawamura M. Angew. Chem. Int. Ed. 2011; 50: 8363
    • 9p Yamamoto T, Morita T, Takagi J, Yamakawa T. Org. Lett. 2011; 13: 5766
    • 9q Huang K, Yu D.-G, Zheng S.-F, Wu Z.-H, Shi Z.-J. Chem. Eur. J. 2011; 17: 786
    • 9r Molander GA, Trice SL. J, Kennedy SM. J. Org. Chem. 2012; 77: 8678
    • 9s Chow WK, Yuen OY, Choy PY, So CM, Lau CP, Wong WT, Kwong FY. RSC Adv. 2013; 3: 12518
    • 9t Molander GA, Cavalcanti LN, Garcia-Garcia C. J. Org. Chem. 2013; 78: 6427
    • 9u Marciasini LD, Richy N, Vaultier M, Pucheault M. Adv. Synth. Catal. 2013; 355: 1083
    • 9v Bose SK, Marder TB. Org. Lett. 2014; 16: 4562
    • 9w Zarate C, Manzano R, Martin R. J. Am. Chem. Soc. 2015; 137: 6754
    • 9x Frank R, Howell J, Campos J, Tirfoin R, Phillips N, Zahn S, Mingos DM. P, Aldridge S. Angew. Chem. Int. Ed. 2015; 54: 9586
    • 9y Bhanuchandra M, Baralle A, Otsuka S, Nogi K, Yorimitsu H. Org. Lett. 2016; 18: 2966
    • 10a Chen K, Zhang S, He P, Li P. Chem. Sci. 2016; 7: 3676
    • 10b Mfuh AM, Doyle JD, Chherti B, Arman H.-D, Larinov OV. J. Am. Chem. Soc. 2016; 138: 2985
    • 10c Mfuh AM, Schneider BD, Cruces W, Larinov OV. Nat. Protoc. 2017; 12: 604
    • 10d Liu B, Lim C.-H, Miyake GM. J. Am. Chem. Soc. 2017; 139: 13616
  • 11 Liu W, Yang X, Gao Y, Li CJ. J. Am Chem. Soc. 2017; 139: 8621
  • 12 Candish L, Teders M, Glorius F. J. Am. Chem. Soc. 2017; 139: 7440

    • For selected examples, see:
    • 13a Deronzier A, Cano-Yelo H. J. Chem. Soc., Perkin Trans. 2 1984; 1093
    • 13b Hari DP, Schroll P, König B. J. Am. Chem. Soc. 2012; 134: 2958
    • 13c Hari DP, Hering T, König B. Org. Lett. 2012; 14: 5334
    • 13d Xiao T, Dong X, Tang Y, Zhou L. Adv. Synth. Catal. 2012; 354: 3195
    • 13e Schroll P, Hari DP, König B. ChemistryOpen 2012; 1: 130
    • 13f Jiang H, Huang C, Guo J, Zeng C, Zhang Y, Yu S. Chem. Eur. J. 2012; 18: 15158
    • 13g Hering T, Hari DP, König B. J. Org. Chem. 2012; 77: 10347
    • 13h Yu J, Zhang L, Yan G. Adv. Synth. Catal. 2012; 354: 2625
    • 13i Hari DP, Hering T, König B. Angew. Chem. Int. Ed. 2014; 53: 725
    • 13j Jia ZH, Zhao CJ, Zhang YY, Xue D, Wang C, Xiao J. Chem. Eur. J. 2014; 20: 2960
    • 13k Zheng J, Chu J, Zhang X, Lei X. J. Org. Chem. 2014; 79: 10682
    • 13l Mary P, Kundu D, Ranu BC. Eur. J. Org. Chem. 2015; 1727
    • 13m Hopkinson MN, Tlahuxt A, Glorius F. Acc. Chem. Res. 2016; 49: 2261
    • 13n Majek M, von Wangelin JA. Chem. Commun. 2013; 49: 5507
    • 13o Li Y, Xie W, Jiang X. Chem. Eur. J. 2015; 21: 16059
    • 13p Ghosh I, Marzo L, Das A, Shaikh R, König B. Acc. Chem. Res. 2016; 49: 1566
    • 13q Hong B, Lee J, Lee A. Tetrahedron Lett. 2017; 58: 2809
    • 13r Hernández JG. Beilstein J. Org. Chem. 2017; 13: 1463
    • 14a Crespi S, Protti S, Fagnoni M. J. Org. Chem. 2016; 81: 9612
    • 14b Dossena AD, Sampaolesi S, Palmieri A, Protti S, Fagnoni M. J. Org. Chem. 2017; 82: 10687
    • 14c Sauer C, Liu Y, De Nisi A, Protti S, Fagnoni M, Bandini M. ChemCatChem 2017; 9: 4456
    • 14d da Silva Júnior PE, Amin HI. M, Nauth AM, da Silva Emery F, Protti S, Opatz T. ChemPhotoChem 2018; 2: 878
  • 15 During the preparation of this manuscript a similar protocol for the borylation reaction appeared: Xu Y, Yang X, Fang H. J. Org. Chem. 2018; 83: 12831
  • 16 Li Y, Xie W, Jiang X. Chem. Eur. J. 2015; 21: 16059
  • 17 Zhang L, Jiao L. J. Am. Chem. Soc. 2017; 139: 607
  • 18 Chow WK, Yuen OY, So CM, Wong WT, Kwong FY. J. Org. Chem. 2012; 77: 3543
  • 19 Benquing C, Shichong J, Etsuko T, Norimichi S, Norio S. Chem. Commun. 2017; 53: 12738
  • 20 Harrison DJ, Tam NC, Vogels CM, Langler RF, Westcott SA. Tetrahedron Lett. 2004; 45: 8493
  • 21 Majekt M, von Wangelin AJ. Chem. Commun. 2013; 49: 5507
  • 22 Ebenezer JM, Jakob M. Tetrahedron Lett. 2014; 55: 5323
  • 23 Beier P, Pestyrikova T, Vida N, Iakobson G. Org. Lett. 2011; 13: 1466
  • 24 Liu G.-Z, Xu H.-W, Wang P, Lin Z.-T, Duan Y.-C, Zheng J.-X, Liu H.-M. Eur. J. Med. Chem. 2013; 65: 323
  • 25 Gul K, Narayanaperumal S, Dornelles L, Rodriges OE. D, Braga AL. Tetrahedron Lett. 2011; 52: 3592