Synthesis 2017; 49(23): 5149-5158
DOI: 10.1055/s-0036-1588513
paper
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Copper-Free Sonogashira Coupling of 2-Bromoarylcarbonyls: Synthesis of Isobenzofurans via One-Pot Reductive Cyclization

Alavala Gopi Krishna Reddy, Gedu Satyanarayana*
  • Department of Chemistry, Indian Institute of Technology, Hyderabad, Kandi – 502 285, Sangareddy, Telangana, India   Email: gvsatya@iith.ac.in
We are grateful to the Council of Scientific and Industrial Research (CSIR), New Delhi, for the financial support [Sanction No. 02(0262)/16/EMR-11].
Further Information

Publication History

Received: 27 June 2017

Accepted after revision: 29 June 2017

Publication Date:
02 August 2017 (eFirst)

Abstract

Palladium-catalyzed copper-free Sonogashira coupling of 2-bromocarbonyls is presented. This method afforded the 2-alkynylaryl carbonyls, useful synthons for the accomplishment of many carbocyclic and heterocyclic motifs. Significantly, the strategy was extended to the one-pot synthesis of isobenzofurans via reduction followed by intramolecular 5-exo-dig cyclization.

Supporting Information

 
  • References

  • 1 Domaradzki ME. Long Y. She Z. Liu X. Zhang G. Chen Y. J. Org. Chem. 2015; 80: 11360
    • 2a Gobé V. Retailleau P. Guinchard X. Chem. Eur. J. 2015; 21: 17587
    • 2b Danda A. Kumar K. Waldmann H. Chem. Commun. 2015; 51: 7536
    • 2c Martins GM. Zeni G. Back DF. Kaufman TS. Silveira CC. Adv. Synth. Catal. 2015; 357: 3255
    • 3a Zhou P. Hao W.-J. Zhang J.-P. Jiang B. Li G. Tu S.-J. Chem. Commun. 2015; 51: 13012
    • 3b Hu Y. Li Y. Zhang S. Li C. Li L. Zha Z. Wang Z. Org. Lett. 2015; 17: 4018
  • 4 Xiao T. Peng P. Xie Y. Wang Z.-Y. Zhou L. Org. Lett. 2015; 17: 4332
    • 5a Qiao J. Liu B. Liao Z. Li Y. Ma L. Dong C. Zhou H.-B. Tetrahedron 2014; 70: 3782
    • 5b Yang J. Yu X. Wu J. Synthesis 2014; 46: 1362
  • 6 Xu L. Jiang H. Hao J. Zhao G. Tetrahedron 2014; 70: 4373
    • 7a Tomás-Mendivil E. Starck J. Ortuno J.-C. Michelet V. Org. Lett. 2015; 17: 6126
    • 7b Mariaule G. Newsome G. Toullec PY. Belmont P. Michelet V. Org. Lett. 2014; 16: 4570
    • 8a Rastogi UG. K. Ginotra SK. Agarwal A. Tandon V. Org. Biomol. Chem. 2015; 13: 1000
    • 8b Reddy V. Jadhav AS. Anand RV. Org. Biomol. Chem. 2015; 13: 3732
    • 8c Jeganathan M. Pitchumani K. RSC Adv. 2014; 4: 38491
    • 8d Zhang M. Zhang H.-J. Ruan W. Wen T.-B. Eur. J. Org. Chem. 2015; 5914
  • 9 Jha RR. Aggarwal T. Verma AK. Tetrahedron Lett. 2014; 55: 2603
  • 10 Janreddy D. Kavala V. Kotipalli T. Kuo C.-W. Kuo T.-S. Chen M.-L. He C.-H. Yao C.-F. Adv. Synth. Catal. 2014; 356: 3083
  • 11 Guo B. Zhou Y. Zhang L. Hua R. J. Org. Chem. 2015; 80: 7635
  • 12 Manojveer S. Balamurugan R. Chem. Commun. 2014; 50: 9925
  • 13 Debrouwer W. Seigneur RA. J. Heugebaert TS. A. Stevens CV. Chem. Commun. 2015; 51: 729
  • 14 Maurya RA. Adiyala PR. Chandrasekhar D. Reddy CN. Kapure JS. Kamal A. ACS Comb. Sci. 2014; 16: 466
  • 15 Wang J. Zhu H.-T. Li Y.-X. Wang L.-J. Qiu Y.-F. Qiu Z.-H. Zhong M.-j. Liu X.-Y. Liang Y.-M. Org. Lett. 2014; 16: 2236
  • 16 Zhu S. Huang H. Zhang Z. Ma T. Jiang H. J. Org. Chem. 2014; 79: 6113
    • 17a Sonogashira K. Tohda Y. Hagihara N. Tetrahedron Lett. 1975; 44: 4467
    • 17b Cassar LJ. Organomet. Chem. 1975; 93: 253
    • 17c Dieck HA. Heck RF. J. Organomet. Chem. 1975; 93: 259
    • 17d Bellina F. Carpita A. Mannocci L. Rossi R. Eur. J. Org. Chem. 2004; 69: 2610
    • 17e Lemay AB. Vulic KS. Ogilvie WW. J. Org. Chem. 2006; 71: 3615
  • 18 Gelman D. Buchwald SL. Angew. Chem. Int. Ed. 2003; 42: 5993
  • 19 Chinchilla R. Nájera C. Chem. Rev. 2007; 107: 874
    • 20a Sørensen US. Pombo-Villar E. Tetrahedron 2005; 61: 2697
    • 20b Guan JT. Weng TQ. Yu G.-A. Liu SH. Tetrahedron Lett. 2007; 48: 7129
    • 20c Komáromi A. Tolnai GL. Novák Z. Tetrahedron Lett. 2008; 49: 7294
    • 20d Cai M. Xu Q. Sha J. J. Mol. Catal. A: Chem. 2007; 272: 293
    • 20e Komura K. Nakamura H. Sugi Y. J. Mol. Catal. A: Chem. 2008; 273: 72
    • 20f Gu Z. Li Z. Liu Z. Wang Y. Liu C. Xiang J. Catal. Commun. 2008; 9: 2154
    • 20g Liu N. Liu C. Xu Q. Jin Z. Eur. J. Org. Chem. 2011; 4422
    • 20h Ye Z.-W. Yi W.-B. J. Fluorine Chem. 2008; 129: 1124
    • 21a Reddy AG. K. Krishna J. Satyanarayana G. Synlett 2011; 1756
    • 21b Krishna J. Reddy AG. K. Ramulu BV. Mahendar L. Satyanarayana G. Synlett 2012; 23: 375
    • 21c Reddy AG. K. Satyanarayana G. Tetrahedron 2012; 68: 8003
    • 21d Reddy AG. K. Krishna J. Satyanarayana G. Tetrahedron Lett. 2012; 53: 5635
    • 21e Krishna J. Reddy AG. K. Satyanarayana G. Synlett 2013; 24: 967
    • 21f Reddy AG. K. Krishna J. Satyanarayana G. Tetrahedron 2013; 69: 10098
    • 21g Krishna J. Reddy AG. K. Satyanarayana G. Tetrahedron Lett. 2014; 55: 861
    • 21h Krishna J. Reddy AG. K. Satyanarayana G. Synth. Commun. 2014; 44: 2103
    • 21i Mahendar L. Krishna J. Reddy AG. K. Ramulu BV. Satyanarayana G. Org. Lett. 2012; 14: 628
    • 21j Mahendar L. Satyanarayana G. J. Org. Chem. 2014; 79: 2059
    • 21k Reddy AG. K. Satyanarayana G. Synthesis 2015; 47: 1269
    • 21l Krishna J. Reddy AG. K. Satyanarayana G. Adv. Synth. Catal. 2015; 357: 3597
    • 21m Mahendar L. Satyanarayana G. J. Org. Chem. 2015; 80: 7089
    • 21n Krishna J. Niharika P. Satyanarayana G. RSC Adv. 2015; 5: 26749
    • 21o Das A. Reddy AG. K. Krishna J. Satyanarayana G. RSC Adv. 2014; 4: 26662
    • 21p Ramulu BV. Satyanarayana G. RSC Adv. 2015; 5: 70972
    • 21q Niharika P. Satyanarayana G. RSC Adv. 2016; 6: 837
    • 21r Niharika P. Ramulu BV. Satyanarayana G. Org. Biomol. Chem. 2014; 12: 4347
    • 21s Ramulu BV. Niharika P. Satyanarayana G. Synthesis 2015; 47: 1255
    • 21t Kumar DR. Satyanarayana G. Org. Lett. 2015; 17: 5894
    • 21u Suchand B. Krishna J. Ramulu BV. Dibyendu D. Reddy AG. K. Mahendar L. Satyanarayana G. Tetrahedron Lett. 2012; 53: 3861
    • 21v Reddy AG. K. Satyanarayana G. J. Org. Chem. 2016; 81: 12212
    • 21w Reddy AG. K. Krishna J. Satyanarayana G. ChemistrySelect 2016; 1: 1151
  • 22 Mahendar L. Reddy AG. K. Krishna J. Satyanarayana G. J. Org. Chem. 2014; 79: 8566
    • 23a Reddy AG. K. Mahendar L. Satyanarayana G. Synth. Commun. 2014; 44: 2076
    • 23b Ansari IA. Gree R. Org. Lett. 2002; 4: 1507
    • 23c Gamez P. Arends IW. C. E. Reedijk J. Sheldon RA. Chem. Commun. 2003; 2414
    • 23d Liu C. Han J. Wang J. Synlett 2007; 643
    • 23e Figiel PJ. Kopylovich MN. Lasri J. daSilva MF. C. G. daSilva JJ. R. F. Pombeiro AJ. L. Chem. Commun. 2010; 46: 2766
    • 23f Hoover JM. Stahl SS. J. Am. Chem. Soc. 2011; 133: 16901
    • 24a Ruchirawat S. Kittakoop P. J. Nat. Prod. 2010; 74: 79
    • 24b Tsi D. Tan BK. H. Phytother. Res. 1997; 11: 576
    • 24c Miao J. Ge H. Org. Lett. 2013; 15: 2930
    • 24d Holler U. Gloer JB. Wicklow DT. J. Nat. Prod. 2002; 65: 876
    • 24e Harper JK. Arif AM. Ford EJ. Strobel G. Porco J. Tomer DP. Oneill KL. Heider EM. Grant DM. Tetrahedron 2003; 59: 2471
    • 24f Shang XS. Li DY. Li NT. Liu PN. Dyes Pigments 2015; 114: 8
    • 25a Meegalla SK. Rodrigo R. J. Org. Chem. 1991; 56: 1882
    • 25b Azzena U. Demartis S. Fiori MG. Melloni G. Pisano L. Tetrahedron Lett. 1995; 36: 8123
    • 25c Azzena U. Demartis S. Melloni G. J. Org. Chem. 1996; 61: 4913
    • 25d Mikami K. Ohmura H. Org. Lett. 2002; 4: 3355
    • 25e Siyang HX. Wu XR. Liu HL. Wu XY. Liu PN. J. Org. Chem. 2014; 79: 1505
    • 26a Zanardi A. Mata JA. Peris E. Organometallics 2009; 28: 4335
    • 26b Brinkmann C. Barrett AG. M. Hill MS. Procopiou PA. Reid S. Organometallics 2012; 31: 7287
    • 26c Li DY. Shi KJ. Mao XF. Chen GR. Liu PN. J. Org. Chem. 2014; 79: 4602
    • 26d Li DY. Shi KJ. Mao XF. Zhao ZL. Wu XY. Liu PN. Tetrahedron 2014; 70: 7022
    • 26e Buxaderas E. Alonso DA. Nájera C. Adv. Synth. Catal. 2014; 356: 3415
    • 26f Fan YC. Kwon O. Org. Lett. 2012; 14: 3264
    • 26g Lin C.-H. Wang Y.-J. Lee C.-F. Eur. J. Org. Chem. 2010; 4368
  • 27 Lee I.-K. Jang Y.-W. Kim Y.-S. Yu SH. Lee KJ. Park S.-M. Oh B.-T. Chae J.-C. Yun B.-S. J. Antibiotics 2009; 62: 163
  • 28 CCDC 1532096 contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
  • 29 Zheng GZ. Zhizhang LZ. Zhichang LZ. Ying WY. Chengbin LC. Jiannan XJ. Catal. Commun. 2008; 9: 2154