Palladium-Catalyzed Copper-Promoted Hiyama-Type Carbon–­Carbon Cross-Coupling Reactions of Dihetaryl Disulfides as ­Electrophiles

Abstract

Dihetaryl disulfides were used as electrophiles in a palladium-catalyzed carbon–carbon cross-coupling reaction with arylsilanes to ­realize a Hiyama-type reaction. This unique transformation shows high reactivity, excellent functional-group tolerance, and mild reaction conditions, making it an attractive alternative to conventional cross-coupling approaches for carbon−carbon bond construction.

Key words

dihetaryl disulfides - arylsilanes - Hiyama reactions - cross-coupling - platinum catalyst - arylation

• References and Notes

• 1a Gouda K.-i. Hagiwara E. Hatanaka Y. Hiyama T. J. Org. Chem. 1996; 61: 7232
• 1b Molander GA. Lannazzo L. J. Org. Chem. 2011; 76: 9182
• 1c Mino T. Shirae Y. Saito T. Sakamoto M. Fujita T. J. Org. Chem. 2006; 71: 9499
• 1d Raders SM. Kingston JV. Verkade JG. J. Org. Chem. 2010; 75: 1744
• 1e Bi L. Georg GI. Org. Lett. 2011; 13: 5413
• 1f Denmark SE. Sweis RF. J. Am. Chem. Soc. 2004; 126: 4876
• 2a Martin R. Buchwald SL. J. Am. Chem. Soc. 2007; 129: 3844
• 2b Roche AJ. Abboud KA. Dolbier WR. Jr. J. Org. Chem. 2015; 80: 5355
• 2c Hua XY. Masson-Makdissi J. Sullivan RJ. Newman SG. Org. Lett. 2016; 18: 5312
• 2d Phan NT. S. Brown DH. Styring P. Green Chem. 2004; 6: 526
• 2e Netherton MR. Fu GC. Adv. Synth. Catal. 2004; 346: 1525
• 3a Zhao T. Ghosh P. Martinez Z. Liu X. Meng X. Darensbourg MY. Organometallics 2017; 36: 1822
• 3b Stefani HA. Cella R. Vieira AS. Tetrahedron 2007; 63: 3623
• 3c Ke H. Chen X. Zou G. J. Org. Chem. 2014; 79: 7132
• 3d Halima TB. Zhang W. Yalaoui I. Hong X. Yang Y.-F. Houk KN. Newman SG. J. Am. Chem. Soc. 2017; 139: 1311
• 3e Sharma P. Rohilla S. Jain N. J. Org. Chem. 2017; 82: 1105
• 3f Frisch AC. Beller M. Angew. Chem. Int. Ed. 2005; 44: 674
• 3g Woerly EM. Cherney AH. Davis EK. Burke MD. J. Am. Chem. Soc. 2010; 132: 6941
• 4a Hassan J. Sévignon M. Gozzi C. Schulz E. Lemaire M. Chem. Rev. 2002; 102: 1359
• 4b Littke AF. Fu GC. Angew. Chem. Int. Ed. 2002; 41: 4176
• 4c Suzuki T. Watanabe S. Kobayashi S. Tanino KJ. Org. Lett. 2017; 19: 922
• 4d Stille JK. Angew. Chem. Int. Ed. 1986; 25: 508
• 4e Garcia-Martinez JC. Lezutekong R. Crooks RM. J. Am. Chem. Soc. 2005; 127: 5097
• 4f Su W. Urgaonkar S. McLaughlin PA. Verkade JG. J. Am. Chem. Soc. 2004; 126: 16433
• 4g Guo Y. Quan T. Lu Y. Luo T. J. Am. Chem. Soc. 2017; 139: 6815
• 4h Zhou W.-J. Wang K.-H. Wang J.-X. J. Org. Chem. 2009; 74: 5599
• 5a Haraguchi R. Tanazawa S.-g. Tokunaga N. Fukuzawa S.-i. Org. Let. 2017; 19: 1646
• 5b Kienle M. Knochel P. Org. Lett. 2010; 12: 2702
• 5c Liu J. Deng Y. Wang H. Zhang H. Yu G. Wu B. Zhang H. Li Q. Marder TB. Yang Z. Lei A. Org. Lett. 2008; 10: 2661
• 5d Negishi E.-i. Anastasia L. Chem. Rev. 2003; 103: 1979
• 5e Nicolaou KC. Bulger PG. Sarlah D. Angew. Chem. Int. Ed. 2005; 44: 4442
• 5f Tao J.-L. Yang B. Wang Z.-X. J. Org. Chem. 2015; 80: 12627
• 6a Hiyama T. J. Organomet. Chem. 2002; 653: 58
• 6b Hatanaka Y. Goda K.-i. Okahara Y. Hiyama T. Tetrahedron. 1994; 50: 8301
• 6c Hirabayashi K. Mori A. Kawashima J. Suguro M. Nishihara Y. Hiyama T. J. Org. Chem. 2000; 65: 5342
• 6d Nakao Y. Oda T. Sahoo AK. Hiyama T. J. Organomet. Chem. 2003; 687: 570
• 7a Saijo H. Sakaguchi H. Ohashi M. Ogoshi S. Organometallics 2014; 33: 3669
• 7b Pierrat P. Gros P. Fort Y. Org. Lett. 2005; 7: 697
• 8a Yuen OY. So CM. Man HW. Kwong FY. Chem. Eur. J. 2016; 22: 6471
• 8b Zhang S. Cai J. Yamamoto Y. Bao M. J. Org. Chem. 2017; 82: 5974
• 9a Domin D. Benito-Garagorri D. Mereiter K. Froehlich J. Kirchner K. Organometallics 2005; 24: 3957
• 9b Lee J.-Y. Fu GC. J. Am. Chem. Soc. 2003; 125: 5616
• 9c Sakon A. Ii R. Hamasaka G. Uozumi Y. Shinagawa T. Shimomura O. Nomura R. Ohtaka A. Organometallics 2017; 36: 1618
• 9d Dai X. Strotman NA. Fu GC. J. Am. Chem. Soc. 2008; 130: 3302
• 10a Itami K. Kamei T. Yoshida J.-i. J. Am. Chem. Soc. 2003; 125: 14670
• 10b Nakao Y. Imanaka H. Sahoo AH. Yada A. Hiyama T. J. Am. Chem. Soc. 2005; 127: 6952
• 10c Gurung SK. Thapa S. Vangala AS. Giri R. Org. Lett. 2013; 15: 5378
• 10d Nokami T. Tomida Y. Kamei T. Itami K. Yoshida J.-i. Org. Let. 2006; 8: 729
• 11a Zhang L. Wu J. J. Am. Chem. Soc. 2008; 130: 12250
• 11b Cheng K. Wang C. Ding Y. Song Q. Qi C. Zhang X.-M. J. Org. Chem. 2011; 76: 9261
• 11c Shi W.-J. Yu D.-G. Zhao H.-W. Wang Y. Cao Z.-C. Zhang L.-S. Yu D.-G. Shi Z.-J. Adv. Synth. Catal. 2016; 358: 2410
• 11d Chau M. Lee HW. Lau CP. Kwong FY. Org. Lett. 2009; 11: 317
• 11e Zhang L. Qing J. Yang P. Wu J. Org. Lett. 2008; 10: 4971
• 11f Seganish WM. De Shong P. J. Org. Chem. 2004; 69: 1137
• 11g Melvin PR. Hazari N. Beromi MM. Shah HP. Williams MJ. Org. Lett. 2016; 18: 5784
• 12a Liu Y. Wang H. Wang C. Wan J.-P. Wen C. RSC Adv. 2013; 3: 21369
• 12b Du Y. Yang H.-C. Xu X.-L. Wu J. Xu Z.-K. ChemCatChem 2015; 7: 3822
• 12c Wang H. Huang G. Sun Y. Liu Y. J. Chem. Res. 2014; 38: 96
• 12d Wang G. Guo Y. Lü Y. Wang X. Quan Z. Chin. J. Org. Chem. 2016; 36: 1375

For examples of C–C coupling, see:
• 13a Quan Z.-J. Lv Y. Wang X.-C. Jing F.-Q. Jia X.-D. Huo C.-D. Adv. Synth. Catal. 2014; 356: 325
• 13b Du B.-X. Da Y.-X. Zhang Z. Adv. Synth. Catal. 2015; 357: 1270
• 13c Wei K.-J. Quan Z.-J. Zhang Z. Da Y.-X. Wang X.-C. RSC Adv. 2016; 6: 78059

For examples of C–N coupling, see:
• 14a Wei K.-J. Quan Z.-J. Zhang Z. Da Y.-X. Wang X.-C. Synlett 2016; 27: 1743
• 14b Wei K.-J. Quan Z.-J. Zhang Z. Da Y.-X. Wang X.-C. Org. Biomol. Chem. 2016; 14: 2395
• 15 For examples of C–S coupling, see: Guo Y. Quan Z.-J. Da Y.-X. Zhang Z. Wang X.-C. RSC Adv. 2015; 5: 45479
• 16a Kappe CO. Tetrahedron 1993; 49: 6937
• 16b Kappe CO. Eur. J. Med. Chem. 2000; 35: 1043
• 16c Dallinger D. Stadler A. Kappe CO. Pure Appl. Chem. 2004; 76: 1017
• 17 Deres K. Schröder CH. Paessens A. Goldmann S. Hacker HJ. Weber O. Kräemer T. Niewöhner U. Pleiss U. Stoltefuss J. Graef E. Koletzki D. Masantschek RN. A. Reimann A. Jaeger R. Groß R. Beckermann B. Schlemmer K.-H. Haebich D. Rübsamen-Waigmann H. Science 2003; 299: 893
• 18 Ethyl 4-Methyl-2,6-diphenylpyrimidine-5-carboxylate (3a); Typical Procedure A Schlenk tube was charged with disulfide 1a (0.2 mmol, 0.1094 g), Pd(OAc)₂ (3 mol%), CuTC (3.0 equiv), and PCy₃ (6 mol%), and the tube was sealed. PhSi(OMe)₃ (2a; 3.0 equiv, 0.6 mmol, 0.1188 g), TBAF (3.0 equiv, 0.6 mmol), and THF (2 mL) were then injected by syringe into the sealed tube under N₂, and the mixture was stirred at 60 °C for 24 h until the reaction as complete (TLC; silica gel). The mixture was cooled to r.t., the reaction was quenched with sat. aq NH₄Cl (2 mL), and the mixture was extracted with EtOAc (3 × 10 mL). The organic layers were combined, dried (MgSO₄), and concentrated in vacuo, and the resulting residue was purified column chromatography [silica gel, EtOAc–PE (1:50)] to give a white solid; yield: 45 mg (72%); mp 66–67 °C. ¹H NMR (400 MHz, CDCl₃): δ = 8.51–8.49 (m, 2 H), 7.71–7.69 (m, 2 H), 7.44–7.41 (m, 6 H), 4.15 (q, J = 7.2 Hz, 2 H), 2.64 (s, 3 H), 1.03 (t, J = 7.2 Hz, 3 H). ¹³C NMR (100 MHz, CDCl₃): δ = 168.44, 165.40, 163.68, 163.65, 138.23, 137.10, 131.11, 130.04, 128.69, 128.54, 128.52, 128.49, 123.40, 61.82, 22.87, 13.70. HRMS (ESI⁺): m/z [M + H]⁺ Calcd for C₂₀H₁₉N₂O₂: 319.1441; found: 319.1447.
• 19 Ethyl 2-(Benzylthio)-4-methyl-6-phenylpyrimidine-5-carboxylate (8) Oil; yield: 12 mg (16%). ¹H NMR (600 MHz, CDCl₃): δ = 7.63–7.56 (m, 2 H), 7.45–7.43 (m, 3 H), 7.37–7.35 (m, 2 H), 7.20–7.17 (m, 3 H), 4.46 (s, 2 H), 4.16 (q, J = 7.2 Hz, 2 H), 2.57 (s, 3 H), 1.03 (t, J = 7.2 Hz, 3 H). ¹³C NMR (150 MHz, CDCl₃): δ = 170.65, 168.01, 165.60, 163.75, 141.16, 130.05, 129.08, 128.65, 128.40 (2 C), 128.31, 128.28, 127.13, 125.83, 61.70, 35.34, 22.59, 13.58. HRMS (ESI⁺): m/z [M + H]⁺ Calcd for C₂₁H₂₁N₂O₂S: 365.1318; found: 365.1315.