ArticleNo Access

Carbene insertion to N–H bonds of 2-aminothiazole and 2-amino-1,3,4-thiadiazole derivatives catalyzed by iron phthalocyanine

Institut de Recherches sur la Catalyse et l’Environnement de Lyon, IRCELYON, UMR 5256, CNRS, Université Lyon 1, 2 av. Albert Einstein, 69626 Villeurbanne Cedex, France

Search for more papers by this author

Alexander G. Martynov

A.N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Leninskii pr., 31, Bldg. 4, 119071, Moscow, Russia

Search for more papers by this author

Yulia G. Gorbunova

A.N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Leninskii pr., 31, Bldg. 4, 119071, Moscow, Russia

Search for more papers by this author

Aslan Yu. Tsivadze

A.N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Leninskii pr., 31, Bldg. 4, 119071, Moscow, Russia

Search for more papers by this author

, and

Alexander B. Sorokin

Institut de Recherches sur la Catalyse et l’Environnement de Lyon, IRCELYON, UMR 5256, CNRS, Université Lyon 1, 2 av. Albert Einstein, 69626 Villeurbanne Cedex, France

E-mail Address: alexander.sorokin@ircelyon.univ-lyon1.fr

Correspondence to: Alexander Sorokin, tel.: +33 472445337, fax: +33 472445399.

SPP full member in good standing

Search for more papers by this author

https://doi.org/10.1142/S1088424619500354Cited by:5 (Source: Crossref)

Abstract

Iron(III) phthalocyaninate decorated with crown ether substituents, [(15C5)₄PcFe]Cl, efficiently catalyzed the insertion of carbene derived from ethyl diazoacetate to six amines functionalized with thiazole, thiazoline and thiadiazole heterocycles. The reactions were carried out under practical conditions using EDA:amine stoechiometric ratio with 0.05 mol% catalyst loading. Turnover numbers up to 3360 have been achieved. The aminoacid derivatives bearing heterocyclic moieties were obtained under catalytic conditions for the first time with 36–69% yields in the case of single N–H insertion products and up to 77% in the case of double N–H insertion products.

This paper is part of the 2019 Women in Porphyrin Science special issue.

Keywords:

Most comprehensive & up-to-date research on PORPHYRINS
Handbook of Porphyrin Science now available in 46 volumes

References

1. Ford A, Miel H, Ring A, Slattery CN, Maguire AR and McKervey MA . Chem. Rev. 2015; 115: 9981–10080. Crossref, Web of Science, Google Scholar
2. Intrieri D, Carminati DM and Gallo E . In Handbook of Porphyrin Science, Vol. 38, Kadish KM, Smith KM and Guilard R . (Eds.) World Scientific Publishing: Singapore, 2016; pp. 1–99. Google Scholar
3. Lu H, Dzik WI, Xu X, Wojtas L, de Bruin B and Zhang XP . J. Am. Chem. Soc. 2011; 133: 8518–8521. Crossref, Web of Science, Google Scholar
4. Xu X, Wang Y, Cui X, Wojtas L and Zhang XP . Chem. Sci. 2017; 8: 4347–4351. Crossref, Web of Science, Google Scholar
5. Deng QH, Chen J, Huang JS, Chui SS-Y, Zhu N, Li G-Yu and Che C-M . Chem. — Eur. J. 2009; 15: 10707–10712. Crossref, Web of Science, Google Scholar
6. Chan K-H, Guan X, Lo VK-Y and Che C-M . Angew. Chem., Int. Ed. 2014; 53: 2982–2987. Crossref, Web of Science, Google Scholar
7. Anding BJ and Woo LK . Organometallics 2013; 32: 2599–2607. Crossref, Web of Science, Google Scholar
8. Carminati DM, Intrieri D, Caselli A, Le Gac S, Boitrel B, Toma L, Legnani L and Gallo E . Chem. — Eur. J. 2016; 22: 13599–13612. Crossref, Web of Science, Google Scholar
9. Mbuvi HM and Woo LK . Organometallics 2008; 27: 637–645. Crossref, Web of Science, Google Scholar
10. Intrieri D, Carminati DM and Gallo E . Dalton Trans. 2016; 45: 15746–15761. Crossref, Web of Science, Google Scholar
11. Aviv I and Gross Z . Chem. — Eur. J. 2008; 14: 3995–4005. Crossref, Web of Science, Google Scholar
12. Chen Q-C, Saltsman I, Kaushansky A, Xiao Z-Y, Fridman N, Zhan X and Gross Z . Chem. — Eur. J. 2018; 24: 17255–17261. Crossref, Web of Science, Google Scholar
13. Simonneaux G, Le Maux P, Ferrand Y and Rault-Berthelot J . Coord. Chem. Rev. 2006; 250: 2212–2221. Crossref, Web of Science, Google Scholar
14. Abeykoon B, Devic T, Grenèche J-M, Fateeva A and Sorokin AB . Chem. Commun. 2018; 54: 10308–10311. Crossref, Web of Science, Google Scholar
15. Brandenberg OF, Fasan R and Arnold FH . Curr. Opin. Biotechnol. 2017; 47: 102–111. Crossref, Web of Science, Google Scholar
16. Brandenberg OF, Prier CK, Chen K, Knight AM, Wu Z and Arnold FH . ACS Catal. 2018; 8: 2629–2634. Crossref, Web of Science, Google Scholar
17. Coelho PS, Brustad EM, Kannan A and Arnold FH . Science 2013; 339: 307–310. Crossref, Web of Science, Google Scholar
18. Kan SBJ, Lewis RD, Chen K and Arnold FH . Science 2016; 354: 1048–1051. Crossref, Web of Science, Google Scholar
19. Sreenilayam G, Moore EJ, Steck V and Fasan R . Adv. Synth. Catal. 2017; 359: 2076–2089. Crossref, Web of Science, Google Scholar
20. Wolf MW, Vargas DA and Lehnert N . Inorg. Chem. 2017; 56: 5623–5635. Crossref, Web of Science, Google Scholar
21. Srour HF, Le Maux P, Chevance S, Carrié D, Le Yondre N and Simonneaux G . J. Mol. Catal. A: Chem. 2015; 407: 194–203. Crossref, Google Scholar
22. Anding BJ, Dairo TO and Woo LK . Organometallics 2017; 36: 1842–1847. Crossref, Web of Science, Google Scholar
23. Ho C-M, Zhang J-L, Zhou C-Y, Chan O-Y, Yan JJ, Zhang F-Y, Huang J-S and Che C-M . J. Am. Chem. Soc. 2010; 132: 1886–1894. Crossref, Web of Science, Google Scholar
24. Mbuvi HM, Klobukowski ER, Roberts GM and Woo LK . J. Porphyrins Phthalocyanines 2010; 14: 284–292. Link, Web of Science, Google Scholar
25. Sreenilayam G and Fasan R . Chem. Commun. 2015; 51: 1532–1534. Crossref, Web of Science, Google Scholar
26. Wang ZJ, Peck NE, Renata H and Arnold FH . Chem. Sci. 2014; 5: 589–601. Google Scholar
27. Liu H-H, Wang Y, Shu Y-J, Zhou X-G, Wu J and Yan S-Y . J. Mol. Catal. A: Chem. 2006; 246: 49–52. Crossref, Google Scholar
28. Ventura DL and Kubiak II RW . Tetrahedron Lett. 2014; 55: 2715–2717. Crossref, Web of Science, Google Scholar
29. Sorokin AB . Chem. Rev. 2013; 113: 159–176. Crossref, Web of Science, Google Scholar
30. Afanasiev P and Sorokin AB . Acc. Chem. Res. 2016; 49: 583–593. Crossref, Web of Science, Google Scholar
31. Nesterov DS, Nesterova OV, Kopylovich MN and Pombeiro AJL . Mol. Catal. 2018; 459: 8–15. Crossref, Web of Science, Google Scholar
32. Alvarez LX and Sorokin AB . J. Organomet. Chem. 2015; 793: 139–144. Crossref, Web of Science, Google Scholar
33. Kudrik EV and Sorokin AB . J. Mol. Catal. A: Chem. 2017; 426: 499–505. Crossref, Web of Science, Google Scholar
34. Kudrik EV, Afanasiev P, Bouchu D, Millet JMM and Sorokin AB . J. Porphyrins Phthalocyanines 2008; 12: 1078–1089. Link, Web of Science, Google Scholar
35. İşci Ü, Faponle AS, Afanasiev P, Albrieux F, Briois V, Ahsen V, Dumoulin F, Sorokin AB and de Visser SP . Chem. Sci. 2015; 6: 5063–5075. Crossref, Web of Science, Google Scholar
36. Pergrale C and Sorokin AB . C. R. Chim. 2000; 3: 803–810. Web of Science, Google Scholar
37. Zalomaeva OV and Sorokin AB . New J. Chem. 2006; 30: 1768–1773. Crossref, Web of Science, Google Scholar
38. Pérollier C, Pergrale-Mejean C and Sorokin AB . New J. Chem. 2005; 29: 1400–1403. Crossref, Web of Science, Google Scholar
39. İşci Ü, Caner C, Zorlu Y, Gürek AG, Dumoulin F and Ahsen V . Dalton Trans. 2014; 43: 17916–17919. Crossref, Web of Science, Google Scholar
40. Prateeptongkum S, Jovel I, Jackstell R, Vogl N, Weckbecker C and Beller M . Chem. Commun. 2009; 1990–1992. Crossref, Web of Science, Google Scholar
41. Carrión EN, Loas A, Patel HH, Pelmuê M, Ramji K and Gorun SM . J. Porphyrins Phthalocyanines 2018; 22: 1–27. Link, Web of Science, Google Scholar
42. Colomban C, Kudrik EV, Afanasiev P and Sorokin AB . Catal. Today 2014; 235: 14–19. Crossref, Web of Science, Google Scholar
43. Sorokin A, Séris J-L and Meunier B . Science 1995; 268: 1163–1166. Crossref, Web of Science, Google Scholar
44. Colomban C, Kudrik EV, Afanasiev P and Sorokin AB . J. Am. Chem. Soc. 2014; 136: 11321–11330. Crossref, Web of Science, Google Scholar
45. Colomban C, Kudrik EV and Sorokin AB . J. Porphyrins Phthalocyanines 2017; 21: 345–353. Link, Web of Science, Google Scholar
46. Griffin JR, Wendell CI, Garwin JA and White MC . J. Am. Chem. Soc. 2017; 139: 13624–13627. Crossref, Web of Science, Google Scholar
47. Alvarez LX, Kudrik EV and Sorokin AB . Chem. — Eur. J. 2011; 17: 9298–9301. Crossref, Web of Science, Google Scholar
48. Clark JR, Feng K, Sookezian A and White MC . Nat. Chem. 2018; 10: 583–591. Crossref, Web of Science, Google Scholar
49. Paradine SM, Griffin JR, Zhao J, Petronico AL, Miller SM and White MC . Nat. Chem. 2015; 7: 987–994. Crossref, Web of Science, Google Scholar
50. Empel C, Hock KJ and Koenigs RM . Chem. Commun. 2019; 55: 338–341. Crossref, Web of Science, Google Scholar
51. Hirose D, Gazvoda M, Košmrlj and Taniguchi T . Chem. Sci. 2016; 7: 5148–5159. Crossref, Web of Science, Google Scholar
52. Kroitor AP, Cailler LP, Martynov AG, Gorbunova YuG, Tsivadze AYu and Sorokin AB . Dalton Trans. 2017; 46: 15651–15655. Crossref, Web of Science, Google Scholar
53. Gorbunova YuG, Martynov AG and Tsivadze AY . In Handbook of Porphyrin Science. Vol. 24, Kadish KM, Smith KM and Guilard R . (Eds.) World Scientific Publishing: Singapore, 2012; pp. 271–388. Google Scholar
54. Martynov AG, Panova MV, Gorbunova YuG and Tsivadze AY u. Macroheterocycles 2014; 7: 47–54. Crossref, Web of Science, Google Scholar
55. Mihara N, Yamada Y, Furukawa K, Kato T and Tanaka K . Dalton Trans. 2018; 47 7044–7049. Crossref, Web of Science, Google Scholar
56. Safonova EA, Martynov AG, Nefedov SE, Kirakosyan GA, Gorbunova YuG and Tsivadze AYu . Inorg. Chem. 2016; 55: 2450–2459. Crossref, Web of Science, Google Scholar
57. Gorbunova YuG, Grishina AD, Martynov AG, Krivenko TV, Isakova AA, Savel’ev VV, Nefedov SE, Abkhalimov EV, Vannikov AV and Tsivadze AYu . J. Mater. Chem. C 2015; 3: 6692–6700. Crossref, Google Scholar
58. Mishra R, Sharma PK, Verma PK, Tomer I, Mathur G and Dhakad PK . J. Heterocycl. Chem. 2017; 54: 2103–2116. Crossref, Web of Science, Google Scholar
59. Frija LMT, Pombeiro AJL and Kopylovich MN . Coord. Chem. Rev. 2016; 308: 32–55. Crossref, Web of Science, Google Scholar
60. Hu Y, Li CY, Wang XM, Yang YH and Zhu HL . Chem. Rev. 2014; 114: 5572–5610. Crossref, Web of Science, Google Scholar
61. Frija LMT, Pombeiro AJL and Kopylovich MN . Eur. J. Org. Chem. 2017; 2670–2682. Crossref, Web of Science, Google Scholar
62. Werbel LM and Battaglia JK . J. Med. Chem. 1971; 14: 10–16. Crossref, Web of Science, Google Scholar
63. Abdel-Sattar NEA, El-Naggar AM and Abdel-Mottaleb MSA . J. Chem. 2017; https://doi.org/10.1155/2017/4102796. Google Scholar
64. Hirashimaa A, Yoshiia Y and Eto M . Biosci. Biotechnol. Biochem. 1992; 56: 1062–1065. Crossref, Web of Science, Google Scholar
65. Zhu T-H, Wang S-Y, Wang G-N and Ji S-J . Chem. — Eur. J. 2013; 19: 5850–5853. Crossref, Web of Science, Google Scholar
66. Safonova EA, Martynov AG, Zolotarevskii VI, Nefedov SE, Gorbunova YG and Tsivadze AY . Dalton Trans. 2015; 44: 1366–1378. Crossref, Web of Science, Google Scholar
67. Nemykin VN, Tret’yakova IN, Volkov SV, Li VD, Mekhryakova NG, Kaliya OL and Luk’yanets EA . Russ. Chem. Rev. 2000; 69: 325–346. Crossref, Google Scholar
68. Hamama WS, Gouda MA, Abd El-Wahab MH and Zoorob HH . J. Heterocyclic Chem. 2014; 51: 1558–1581. Crossref, Web of Science, Google Scholar
69. Strzemecka L, Maciejewska D and Urbanczyk-Lipkowska Z . J. Mol. Struct. 2003; 648: 107–113. Crossref, Web of Science, Google Scholar
70. Remko M, Walsh OA and Richards WG . Chem. Phys. Lett. 2001; 336: 156–162. Crossref, Web of Science, Google Scholar
71. Chen X, Hu Y and Gao J . J. Mol. Struct. 2013; 1049: 362–367. Crossref, Web of Science, Google Scholar