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Highly chemo/regioselective alkoxycarbonylation of terminal allenes catalyzed by Ru/N-ligand system

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Abstract

The Ru-catalyzed highly selective alkoxycarbonylation of allenes with aliphatic alcohols (also as solvent) allow to produce useful α,β-unsaturated esters in good to excellent yields at 70 °C. Efficient regioselectivity could be controlled in the presence of N-ligands while the P-ligands had no influence on the conversion of substrates and the chemo/regioselectivity of target products. By involving N-ligand 4,7-dimethyl-1,10-phenanthroline in the catalytic system, α,β-unsaturated esters were obtained with high conversion and chemo/regioselectivity (conversion up to 99%, chemical selectivity up to 99%, regioselectivity of branched ester/linear ester up to 89/11).

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Data availability

The data that support the findings of this study are available in Supporting Information. Supporting Information associated with this article can be found, in the online version, at https://doi.org/10.1007/s00706-023-03117-9.

References

  1. Wu XF, Fang XJ, Wu LP, Jackstell R, Neumann H, Beller M (2014) Acc Chem Res 47:1041

    Article  CAS  PubMed  Google Scholar 

  2. Yin ZP, Xu JX, Wu XF (2020) ACS Catal 10:6510

    Article  CAS  Google Scholar 

  3. Sumino S, Fusano A, Fukuyama T, Ryu I (2014) Acc Chem Res 47:1563

    Article  CAS  PubMed  Google Scholar 

  4. Markovič A, Lopatka P, Koóš P, Gracza T (2015) Org Lett 17:5618

    Article  PubMed  Google Scholar 

  5. Ismael A, Gevorgyan A, Skrydstrup T, Bayer A (2020) Org Process Res Dev 24:2665

    Article  CAS  Google Scholar 

  6. Goanvic LL, Couturier J, Duboisc J, Carpentier J (2016) J Mol Catal A Chem 417:116

    Article  Google Scholar 

  7. Pongrácz P, Szentjóbi H, Tóth T, Huszthy P, Kollár L (2017) Mol Catal 439:128

    Article  Google Scholar 

  8. Rodrigues C, Delolo FG, Norinder J, Börner A, Bogado AL, Batista AA (2017) J Mol Catal A Chem 426:586

    Article  CAS  Google Scholar 

  9. Diéguez M, Pàmies O, Ruiz A, Diaz Y, Castillón S, Claver C (2004) Coord Chem Rev 248:2165

    Article  Google Scholar 

  10. Gehrtz PH, Hirschbeck V, Fleischer I (2015) Chem Commun 51:12574

    Article  CAS  Google Scholar 

  11. Zhu FX, Wu XF (2011) Org Lett 13:3285

    Article  Google Scholar 

  12. Liu JW, Dong KW, Franke R, Neumann H, Jackstell R, Beller M (2018) Chem Commun 54:12238

    Article  CAS  Google Scholar 

  13. Konrad TM, Fuentes JA, Slawin AMZ, Clarke ML (2010) Angew Chem Int Ed 49:9197

    Article  CAS  Google Scholar 

  14. Hajra S, Bhowmick M, Sinha D (2006) J Org Chem 71:9237

    Article  CAS  PubMed  Google Scholar 

  15. Nemoto T, Ohshima T, Shibasaki M (2001) J Am Chem Soc 123:9474

    Article  CAS  PubMed  Google Scholar 

  16. Matsuo J, Aizawa Y (2005) Tetrahedron Lett 46:407

    Article  CAS  Google Scholar 

  17. Kajitani M, Kamiya I, Nomoto A, Kihara N, Ogawa A (2006) Tetrahedron 62:6355

    Article  CAS  Google Scholar 

  18. Alper H, Hartstock FW, Despeyroux B (1984) J Chem Soc Chem Commun 905

  19. Bai T, Ma S, Jia G (2009) Coord Chem Rev 253:423

    Article  CAS  Google Scholar 

  20. Sam B, Breit B, Krische MJ (2015) Angew Chem Int Ed 54:3267

    Article  CAS  Google Scholar 

  21. Zimmer R, Dinesh CU, Nandanan E, Khan FA (2000) Chem Rev 100:3067

    Article  CAS  PubMed  Google Scholar 

  22. Alcaide B, Almendros P (2004) Eur J Org Chem 16:3377

    Article  Google Scholar 

  23. Pato DJ (1984) Tetrahedron 40:2805

    Article  Google Scholar 

  24. Jeganmohan M, Cheng CH (2008) Chem Commun 27:3101

    Article  Google Scholar 

  25. Guo H, Ma SM (2008) Adv Synth Catal 350:1213

    Article  CAS  Google Scholar 

  26. Bates RW, Satcharoen V (2002) Chem Soc Rev 31:12

    Article  CAS  PubMed  Google Scholar 

  27. Spencer WT, Levin MD, Frontier A (2011) J Org Lett 13:414

    Article  CAS  Google Scholar 

  28. Sam B, Luong T, Krische MJ (2015) Angew Chem Int Ed 54:5465

    Article  CAS  Google Scholar 

  29. Liu JW, Han ZB, Wang XM, Wang Z, Ding KL (2015) J Am Chem Soc 137:15346

    Article  CAS  PubMed  Google Scholar 

  30. Oda S, Sam B, Krische MJ (2015) Angew Chem Int Ed 54:8525

    Article  CAS  Google Scholar 

  31. Okuro K, Alper H (1997) J Org Chem 62:1566

    Article  CAS  Google Scholar 

  32. Geng HQ, Hou CY, Wang LC, Peng JB, Wu XF (2020) J Catal 381:271

    Article  CAS  Google Scholar 

  33. Geng HQ, Peng JB, Wu XF (2019) Org Lett 21:8215

    Article  CAS  PubMed  Google Scholar 

  34. Geng HQ, Wang LC, Hou CY, Wu XF (2020) Org Lett 22:1160

    Article  CAS  PubMed  Google Scholar 

  35. Grigg R, Liu A, Shaw D, Suganthan S, Woodall DE, Yoganathan G (2000) Tetrahedron Lett 41:7125

    Article  CAS  Google Scholar 

  36. Liu J, Liu Q, Franke R, Jackstell R, Beller M (2015) J Am Chem Soc 137:8556

    Article  CAS  PubMed  Google Scholar 

  37. Xiao WJ, Vasapollo G, Alper H (1998) J Org Chem 63:2609

    Article  CAS  PubMed  Google Scholar 

  38. Kodama S, Nishinaka E, Nomoto A, Sonoda M, Ogawa A (2007) Tetrahedron Lett 48:6312

    Article  CAS  Google Scholar 

  39. Köpfer A, Breit B (2015) Angew Chem Int Ed 54:6913

    Article  Google Scholar 

  40. Yoneda E, Kaneko T, Zhang SW, Onitsuka K, Takahashi S (2000) Org Lett 2:441

    Article  CAS  PubMed  Google Scholar 

  41. Zhou DY, Yoneda E, Onitsuka K, Takahashi S (2002) Chem Commun 23:2868

    Article  Google Scholar 

  42. Crabbé P, Fillion H, André D, Luche JL (1979) J Chem Soc Chem Commun 19:859

    Article  Google Scholar 

  43. Kuang J, Ma SM (2009) J Org Chem 74:1763

    Article  CAS  PubMed  Google Scholar 

  44. Kitagaki S, Komizu M, Mukai C (2011) Synlett 8:1129

    Article  Google Scholar 

  45. Kawatsura M, Namioka J, Kajita K, Yamamoto M, Tsuji H, Itoh T (2018) Org Lett 20:3422

    Article  Google Scholar 

  46. Bai YY, Lin ZY, Ye ZY, Dong D, Wang J, Chen L, Xie F, Li YB, Dixneuf PH, Zhang M (2022) Org Lett 24:7988

    Article  CAS  PubMed  Google Scholar 

  47. Ahmad S, Behl M (2019) Chem Eur J 25:11625

    Article  CAS  PubMed  Google Scholar 

  48. Yu SC, Ma SM (2012) Angew Chem Int Ed 51:3074

    Article  CAS  Google Scholar 

  49. Rast S, Modec B, Stephan M, Mohar B (2016) Org Biomol Chem 14:2112

    Article  CAS  PubMed  Google Scholar 

  50. Ye ZR, Huang X, Shao YX, Jiang JX, Qu LB, Zhao CY, Ke ZF (2019) Catal Sci Technol 9:2315

    Article  CAS  Google Scholar 

  51. Saha R, Mukherjee A, Bhattacharya S (2020) Eur J Inorg Chem 48:4539

    Article  Google Scholar 

  52. Tyagi D, Rai RK, Mobin SM, Singhm SK (2017) Asian J Org Chem 6:1647

    Article  CAS  Google Scholar 

  53. Fleischer I, Wu LP, Profir I, Jackstell R, Franke R, Beller M (2013) Chem Eur J 19:10589

    Article  CAS  PubMed  Google Scholar 

  54. Sanchez-Delgado RA, Bradley JS, Wilkinson G (1976) J Chem Soc Dalton Trans 399

  55. Gordon EM, Eisenberg R (1986) J Organomet Chem 306:C53

    Article  CAS  Google Scholar 

  56. Liu Q, Wu LP, Jackstell R, Beller M (2014) ChemCatChem 6:2805

    Article  CAS  Google Scholar 

  57. Mitsudo T, Suzuki N, Kobayashi T, Kondo T (1999) J Mol Catal A Chem 137:253

    Article  CAS  Google Scholar 

  58. Ghaffar T, Adams H, Maitlis PM, Haynes A, Ghaffar T, Adams H, Sunley GJ, Baker MJ (1998) Chem Comm 9:1023

    Article  Google Scholar 

  59. Cheong M, Schmid R, Ziegler T (2000) Organometallics 19:1973

    Article  CAS  Google Scholar 

  60. Kovacs I, Ungvary F, Marko L (1986) Organometallics 5:209

    Article  CAS  Google Scholar 

  61. Sakai N, Mano S, Nozaki K, Takaya H (1993) J Am Chem Soc 115:7033

    Article  CAS  Google Scholar 

  62. Krishnan VV, Suib SL, Corbin DR, Schwarz S, Jones GA (1996) Chem Comm 3:395

    Article  Google Scholar 

  63. Higashizima T, Sakai N, Nozaki K, Takaya H (1994) Tetrahydron Lett 35:2023

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was financially supported by the National Natural Science Foundation of China (No. 21901250).

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Authors and Affiliations

  1. Shandong Chambroad Petrochemicals Co., Ltd, Binzhou, 256500, Shandong, China

    Peng Wang, Huibing Shi, Baolin Feng & Deming Zhao

  2. School of Life Sciences, Henan University, Kaifeng, 475004, Henan, China

    Haigang Wu

  3. School of Biomedical Engineering, Shanghai Jiao Tong University, Shanghai, 200240, China

    Haigang Wu

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  1. Peng Wang
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  2. Huibing Shi
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  3. Baolin Feng
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  4. Deming Zhao
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  5. Haigang Wu
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Correspondence to Peng Wang or Haigang Wu.

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Wang, P., Shi, H., Feng, B. et al. Highly chemo/regioselective alkoxycarbonylation of terminal allenes catalyzed by Ru/N-ligand system. Monatsh Chem 154, 1189–1195 (2023). https://doi.org/10.1007/s00706-023-03117-9

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  • DOI: https://doi.org/10.1007/s00706-023-03117-9

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