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Synlett 2017; 28(13): 1558-1563
DOI: 10.1055/s-0036-1588728
DOI: 10.1055/s-0036-1588728
cluster
Photoinduced Oxidative Cross-Coupling for O–S Bond Formation: A Facile Synthesis of Alkyl Benzenesulfonates
Further Information
Publication History
Received: 10 January 2017
Accepted after revision: 30 January 2017
Publication Date:
28 February 2017 (online)
Abstract
We have developed a photoinduced oxidative cross-coupling of thiophenols with alcohols for O–S bond formation. The protocol uses visible light, a metal-free photocatalyst, and oxygen as the oxidant for the selective synthesis of alkyl benzenesulfonates; no ligand co-additive is necessary. Mechanistic studies suggested that the disulfide and alkyl benzenesulfinate are involved as intermediates and that the transformation proceeds by a radical pathway.
Key words
photoredox catalysis - alkyl benzenesulfonates - C–S bond formation - dioxygen - oxidative coupling.Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588728.
- Supporting Information
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References and Notes
- 1a New Trends in Cross-Coupling: Theory and Applications. Colacot T. RSC; Cambridge: 2015
- 1b Metal-Catalyzed Cross-Coupling Reactions and More. de Meijere A. Oestreich M. Wiley-VCH; Weinheim: 2014
- 1c Metal-Catalyzed Cross-Coupling Reactions. de Meijere A. Diederich F. Wiley-VCH; Weinheim: 2004. 2nd ed., Vol. 2
- 1d Johansson Seechurn CC. C. Kitching MO. Colacot TJ. Snieckus V. Angew. Chem. Int. Ed. 2012; 51: 5062
- 1e Lee C.-F. Liu Y.-C. Badsara SS. Chem. Asian J. 2014; 9: 706
- 1f Liu C. Zhang H. Shi W. Lei A. Chem. Rev. 2011; 111: 1780
- 2a Liu C. Yuan J. Gao M. Tang S. Li W. Shi R. Lei A. Chem. Rev. 2015; 115: 12138
- 2b Zhang G. Liu C. Yi H. Meng Q. Bian C. Chen H. Jian J.-X. Wu L.-Z. Lei A. J. Am. Chem. Soc. 2015; 137: 9273
- 2c Liu C. Liu D. Lei A. Acc. Chem. Res. 2014; 47: 3459
- 2d Girard SA. Knauber T. Li C.-J. Angew. Chem. Int. Ed. 2014; 53: 74
- 2e Wang J. Liu C. Yuan J. Lei A. Angew. Chem. Int. Ed. 2013; 52: 2256
- 2f Liu Q. Jackstell R. Beller M. Angew. Chem. Int. Ed. 2013; 52: 13871
- 2g Liu D. Liu C. Li H. Lei A. Angew. Chem. Int. Ed. 2013; 52: 4453
- 2h Zhang C. Tang C. Jiao N. Chem. Soc. Rev. 2012; 41: 3464
- 2i Chen M. Zheng X. Li W. He J. Lei A. J. Am. Chem. Soc. 2010; 132: 4101
- 2j Zhao Y. Wang H. Hou X. Hu Y. Lei A. Zhang H. Zhu L. J. Am. Chem. Soc. 2006; 128: 15048
- 2k Li Z. Li C.-J. J. Am. Chem. Soc. 2004; 126: 11810
- 3 Schenck GO. Krauch CH. Angew. Chem. 1962; 74: 510
- 4a Straight RC. Spikes JD. In Singlet O2 . Vol. IV. Frimer AA. Chap. 2 CRC Press; Boca Raton: 1985: 91
- 4b Gu C.-L. Foote CS. Kacher ML. J. Am. Chem. Soc. 1981; 103: 5949
- 4c Gu C.-L. Foote CS. J. Am. Chem. Soc. 1982; 104: 6060
- 4d Liang J.-J. Gu C.-L. Kacher ML. Foote CS. J. Am. Chem. Soc. 1983; 105: 4717
- 4e Jensen F. Foote CS. J. Am. Chem. Soc. 1987; 109: 1478
- 4f Sawaki Y. Ogata Y. J. Am. Chem. Soc. 1981; 103: 5947
- 4g Takata T. Tamura Y. Ando W. Tetrahedron 1985; 41: 2133
- 4h Akasaka T. Ando W. Tetrahedron Lett. 1985; 26: 5049
- 4i Clennan EL. Chen X. J. Am. Chem. Soc. 1989; 111: 5787
- 4j Ando W. Kabe Y. Miyazaki H. Photochem. Photobiol. 1980; 31: 191
- 4k Ando W. Takata T. In Singlet O2 . Vol. III, Part 2. Frimer AA. CRC Press; Boca Raton: 1985: 1
- 5a Organic Chemistry of Sulfur. Oae S. Plenum Press; New York: 1977
- 5b Block E. Reactions of Organosulfur Compounds. Academic Press; New York: 1978
- 6 Sysak PK. Foote CS. Ching T.-Y. Photochem. Photobiol. 1977; 26: 19
- 7a Banchereau E. Lacomhe S. Ollivier J. Tetrahedron Lett. 1995; 36: 8197
- 7b Robert-Banchereau E. Lacombe S. Ollivier J. Tetrahedron 1997; 53: 2087
- 7c Baciocchi E. Crescenzi C. Lanzalunga O. Tetrahedron 1997; 53: 4469
- 7d Lacombe S. Cardy H. Simon M. Khoukh A. Soumillion JP. Ayadim M. Photochem. Photobiol. Sci. 2002; 1: 347
- 7e Sheu C. Foote CS. Gu C.-L. J. Am. Chem. Soc. 1992; 114: 3015
- 7f Jensen F. J. Org. Chem. 1992; 57: 6478
- 7g Lacombe S. Loudet M. Dargelos A. Robert-Banchereau E. J. Org. Chem. 1998; 63: 2281
- 7h Memarian HR. Mohammadpoor-Baltork I. Bahrami K. Bull. Korean Chem. Soc. 2006; 27: 106
- 7i Lakkaraju PS. Zhou D. Roth HD. J. Chem. Soc., Perkin Trans. 2 1998; 1119
- 7j Albini A. Bonesi SM. J. Photosci. 2003; 10: 1
- 7k Baciocchi E. Del Giacco T. Ferrero MI. Rol C. Sebastiani GV. J. Org. Chem. 1997; 62: 4015
- 7l Clennan EL. Zhou W. Chan J. J. Org. Chem. 2002; 67: 9368
- 7m Latour V. Pigot T. Simon M. Cardy H. Lacombe S. Photochem. Photobiol. Sci. 2005; 4: 221
- 7n Clennan EL. Acc. Chem. Res. 2001; 34: 875
- 8a Larock RC. Comprehensive Organic Transformations: A Guide to Functional Group Preparations. Wiley-VCH; Weinheim: 1997
- 8b Horning JE. C. In Synthetic Organic Chemistry. Vol. 3. Wagner RB. Zokk HD. Wiley; New York: 1953
- 8c Sandler SR. Karo W. Organic Functional Group Preparations. Academic; New York: 1983. 2nd ed., Vol. 1
- 8d Kabalka GW. Varma M. Varma RS. Srivastava PC. Knapp Jr. FF. J. Org. Chem. 1986; 51: 2386
- 8e Cragg PJ. A Practical Guide to Supramolecular Chemistry. Wiley; Chichester: 2005
- 9a Kurita K. Chem. Ind. (London) 1974; 345
- 9b Yoshida Y. Sakakura Y. Aso N. Okada S. Tanabe Y. Tetrahedron 1999; 55: 2183
- 9c Hartung J. Hünig S. Kneuer R. Schwarz M. Wenner H. Synthesis 1997; 1433
- 9d O’Connell JF. Rapoport H. J. Org. Chem. 1992; 57: 4775
- 9e Katritzky AR. Zhang G. Wu J. Synth. Commun. 1994; 24: 205
- 9f Kazemi F. Massah AR. Javaherian M. Tetrahedron 2007; 63: 5083
- 9g Asano K. Matsubara S. Org. Lett. 2009; 11: 1757
- 9h Karaman R. Leader H. Goldblum A. Breuer E. Chem. Ind. (London) 1987; 857
- 9i Klamann D. Weyerstahl P. Chem. Ber. 1965; 98: 2070
- 9j Nitta Y. Arakawa Y. Chem. Pharm. Bull. 1985; 33: 1380
- 9k Mukaiyama T. Hojo K. Chem. Lett. 1976; 893
- 9l Choudary BM. Chowdari NS. Kantam ML. Tetrahedron 2000; 56: 7291
- 9m Das B. Reddy VS. Reddy MR. Tetrahedron Lett. 2004; 45: 6717
- 9n Velusamy S. Kiran JS. K. Punniyamurthy T. Tetrahedron Lett. 2004; 45: 203
- 9o Comagic S. Schirrmacher R. Synthesis 2004; 885
- 9p Morita J. Nakatsuji H. Misaki T. Tanabe Y. Green Chem. 2005; 7: 711
- 9q Morita J.-i. Nakatsuji H. Misaki T. Tanabe Y. Adv. Synth. Catal. 2006; 348: 2057
- 10a Yoon TP. Ischay MA. Du J. Nat. Chem. 2010; 2: 527
- 10b Sun C.-L. Shi Z.-J. Chem. Rev. 2014; 114: 9219
- 10c Shi L. Xia W. Chem. Soc. Rev. 2012; 41: 7687
- 10d Prier CK. Rankic DA. MacMillan DW. C. Chem. Rev. 2013; 113: 5322
- 10e Xie Z. Wang C. deKrafft KE. Lin W. J. Am. Chem. Soc. 2011; 133: 2056
- 10f Xie J. Xue Q. Jin H. Li H. Cheng Y. Zhu C. Chem. Sci. 2013; 4: 1281
- 10g Liu J. Liu Q. Yi H. Qin C. Bai R. Qi X. Lan Y. Lei A. Angew. Chem. Int. Ed. 2014; 53: 502
- 10h Ischay MA. Anzovino ME. Du J. Yoon TP. J. Am. Chem. Soc. 2008; 130: 12886
- 10i Dirocco DA. Rovis T. J. Am. Chem. Soc. 2012; 134: 8094
- 10j Deng G.-B. Wang Z.-Q. Xia J.-D. Qian P.-C. Song R.-J. Hu M. Gong L.-B. Li J.-H. Angew. Chem. Int. Ed. 2013; 52: 1535
- 10k Cherevatskaya M. Neumann M. Füldner S. Harlander C. Kümmel S. Dankesreiter S. Pfitzner A. Zeitler K. König B. Angew. Chem. Int. Ed. 2012; 51: 4062
-
10l
Cai S.
Zhao X.
Wang X.
Liu Q.
Li Z.
Wang DZ.
Angew. Chem. Int. Ed. 2012; 51: 8050
- 10m Wang K. Meng L.-G. Zhang Q. Wang L. Green Chem. 2016; 18: 2864
- 11a Fukuzumi S. Ohkubo K. Chem. Sci. 2013; 4: 561
- 11b Fukuzumi S. Ohkubo K. Org. Biomol. Chem. 2014; 12: 6059
- 12 Alkyl Benzenesulfonates 3; General Procedure An oven-dried Schlenk tube equipped with a magnetic stirrer bar was charged with Acr+–Mes ClO4 – (5.0 mol%), capped with a septum, and evacuated. A balloon filled with O2 was connected to the Schlenk tube through the side arm, and thiophenol 1(1.0 mmol) and alcohol 2 (3.0 mL) were successively injected into the reaction tube. The mixture was irradiated with light from blue LEDs (3.0 W) and vigorously stirred at r.t. for 18–72 h (see Scheme 2). When the reaction was complete (TLC), the product was purified by flash column chromatography (silica gel, PE–EtOAc).