Development of Molecular Complexity through Nitrene-Transfer Reactions Catalyzed by Copper and Silver Scorpionate Complexes

Manuel R. Rodríguez; M. Mar Díaz-Requejo; Pedro J. Pérez

doi:10.1055/s-0040-1706534

Synlett, Inhaltsverzeichnis

Synlett 2021; 32(08): 763-774
DOI: 10.1055/s-0040-1706534

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Development of Molecular Complexity through Nitrene-Transfer Reactions Catalyzed by Copper and Silver Scorpionate Complexes

Manuel R. Rodríguez

,

M. Mar Díaz-Requejo ∗

Laboratorio de Catálisis Homogénea, Unidad Asociada al CSIC, CIQSO-Centro de Investigación en Química Sostenible and Departamento de Química, Universidad de Huelva, 21007 Huelva, Spain eMail: perez@dqcm.uhu.es eMail: mmdiaz@dqcm.uhu.es

,

Pedro J. Pérez ∗

Laboratorio de Catálisis Homogénea, Unidad Asociada al CSIC, CIQSO-Centro de Investigación en Química Sostenible and Departamento de Química, Universidad de Huelva, 21007 Huelva, Spain eMail: perez@dqcm.uhu.es eMail: mmdiaz@dqcm.uhu.es

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Abstract

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Abstract

For years, metal–nitrene-transfer reactions have been mainly directed toward C=C bond aziridination or C–H bond amidation reactions. In the last decade, multiple efforts have been made to develop new synthetic approaches to expand the applicability of this powerful tool, resulting in the synthesis of complex structures from relatively simple starting materials. Here, we present our contributions to the area with several novel and, to some degree, unexpected transformations developed by our research group. The catalysts for these nitrene-transfer reactions are copper or silver complexes bearing hydrotrispyrazolyl (scorpionate) ligands. These transformations have contributed to an expansion of the scope of organic compounds accessible by nitrene-transfer reactions and to an understanding of the reactivity of metallonitrene species toward the oxidation of less-explored organic substrates.

1 Introduction

2 Synthesis of 1,2-Dihydropyridines from Furans

3 Regio- and Stereoselective Aziridination of Dienes

4 Chemoselective Synthesis of Aminimides from Amines

5 Synthesis of Sulfinamides and Isothiazoles from Alkynes

6 Formation of Azetidines and Methylene Aziridines from Allenes

7 Conclusion

Key words - nitrene transfer - C–N bond formation - copper catalysis - silver catalysis - dihydropyridines - aminimides

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Referenzen

References
1 Kwart H, Khan AA. J. Am. Chem. Soc. 1967; 89: 1951

2a Dequirez G, Pons V, Dauban P. Angew. Chem. Int. Ed. 2012; 51: 7384
2b Degennaro L, Trinchera P, Luisi R. Chem. Rev. 2014; 114: 7881
2c Chang JW. W, Ton TM. U, Chan PW. H. Chem. Rec. 2011; 11: 331
2d Díaz-Requejo MM, Caballero A, Fructos MR, Pérez PJ. In Alkane C–H Activation by Single-Site Metal Catalysis . Pérez PJ. Springer; Dordrecht: 2012. 229
2e Zalatan DN, Du Bois J. Top. Curr. Chem. 2010; 292: 347

3a Breslow DS, Sloan MF. Tetrahedron Lett. 1968; 5349
3b Groves JT, Takahashi T. J. Am. Chem. Soc. 1983; 105: 2073
3c Mansuy D, Mahy J.-P, Dureault A, Bedi G, Battioni P. J. Chem. Soc. Chem. Commun. 1984; 1161
3d Evans DA, Faul MM, Bilodeau MT. J. Org. Chem. 1991; 56: 6744
3e Breslow R, Gellman SH. J. Am. Chem. Soc. 1983; 105: 6728

4 Pérez PJ, Brookhart M, Templeton JL. Organometallics 1993; 12: 261
5 Mairena MA, Díaz-Requejo MM, Belderraín TR, Nicasio MC, Trofimenko S, Pérez PJ. Organometallics 2003; 23: 253
6 Díaz-Requejo MM, Belderraín TR, Nicasio MC, Trofimenko S, Pérez PJ. J. Am. Chem. Soc. 2003; 125: 12078
7 Fructos MR, Trofimenko S, Mar Díaz-Requejo M, Pérez PJ. J. Am. Chem. Soc. 2006; 128: 11784
8 Gómez-Emeterio BP, Urbano J, Díaz-Requejo MM, Pérez PJ. Organometallics 2008; 27: 4126

9a Novác J, Sorm F. Collect. Czech. Chem. Commun. 1958; 23: 1126
9b Caballero A, Díaz-Requejo MM, Trofimenko S, Belderraín TR, Pérez PJ. J. Org. Chem. 2005; 70: 6101
9c Kobayashi Y, Katsuno H, Sato F. Chem. Lett. 1983; 1771
9d Adger BM, Barrett C, Brennan J, McKervey MA, Murray RW. J. Chem. Soc., Chem. Commun. 1991; 1553

10a Floyd MB. J. Org. Chem. 1978; 43: 1641
10b Elliott BJ. D, Hetmanski M, Stoodley RJ, Palfreyman MN. J. Chem. Soc., Perkin Trans. 1 1981; 1782

11 Fructos MR, Álvarez E, Díaz-Requejo MM, Pérez PJ. J. Am. Chem. Soc. 2010; 132: 4600
12 Hogg JL, Jenks DA, Jenks WP. J. Am. Chem. Soc. 1977; 99: 4772
13 Maestre L, Fructos MR, Díaz-Requejo MM, Pérez PJ. Organometallics 2012; 31: 7839−7843

14a Llavería J, Beltrán A, Díaz-Requejo MM, Matheu MI, Castillón S, Pérez PJ. Angew. Chem. Int. Ed. 2010; 49: 7092
14b Llavería J, Beltrán A, Sameera WM. C, Locati A, Díaz-Requejo MM, Matheu MI, Castillón S, Maseras F, Pérez PJ. J. Am. Chem. Soc. 2014; 136: 5342

15a Ma L, Du D.-M, Xu J. Chirality 2006; 18: 575
15b Sureshkumar D, Maity S, Chandrasekaran S. J. Org. Chem. 2006; 71: 1653
15c Knight JG, Muldowney MP. Synlett 1995; 949
15d Piangiolino C, Gallo E, Caselli A, Fantauzzi S, Ragaini F, Cenini S. Eur. J. Org. Chem. 2007; 743
15e Nishimura M, Minakata S, Thongchant S, Ryu I, Komatsu M. Tetrahedron Lett. 2000; 41: 7089

16a Somfai P, Panknin O. Synlett 2007; 1190
16b Ohno H. In Aziridines and Epoxides in Organic Synthesis . Yudin AK. Wiley-VCH; Weinheim: 2006. 37
16c Sweeney JB. Chem. Soc. Rev. 2002; 31: 247
16d McCoull W, Davis FA. Synthesis 2000; 1347

17a Atkinson RS, Kelly BJ. J. Chem. Soc., Chem. Commun. 1988; 624
17b Atkinson RS, Kelly BJ, McNicolas C. J. Chem. Soc., Chem. Commun. 1989; 562
17c Atkinson RS, Williams PJ. J. Chem. Soc., Perkin Trans. 1 1996; 1951
17d Atkinson RS, Ulukanli S, Williams PJ. J. Chem. Soc., Perkin Trans. 1 1999; 2121
17e Cakici M, Karabuga S, Kilic H, Ulukanli S, Şahin E, Sevin F. J. Org. Chem. 2009; 74: 9452

18 Maestre L, Sameera WM. C, Díaz-Requejo MM, Maseras F, Pérez PJ. J. Am. Chem. Soc. 2013; 135: 1338−1348
19 Maestre L, Dorel R, Pablo Ó, Escofet I, Sameera WM. C, Álvarez E, Maseras F, Díaz-Requejo MM, Echavarren AM, Pérez PJ. J. Am. Chem. Soc. 2017; 139: 2216

20a Jain SL, Sharma VB, Sain B. Tetrahedron Lett. 2003; 44: 4385
20b Ochiai M, Kawano Y, Kaneaki T, Tada N, Miyamoto K. Org. Lett. 2009; 11: 281
20c Ochiai M, Miyamoto K, Hayashi S, Nakanishi W. Chem. Commun. 2010; 46: 511
20d Pujari SA, Guénée L, Lacour J. Org. Lett. 2013; 15: 3930

21a McKillip WJ, Sedor EA, Culbertson BM, Wawzonek S. Chem. Rev. 1973; 73: 255
21b Rademacher P. In Science of Synthesis, Vol. 40b. Enders D, Schaumann E. Thieme; Stuttgart: 2009. 1133

For examples, see:

22a Peisach E, Casbier D, Gallion SL, Furth P, Petsko G, Hogan JC. Jr, Ringe D. Science 1995; 269: 66
22b Gangapuram M, Redda KK. J. Heterocycl. Chem. 2009; 46: 309

23 Rodríguez MR, Beltrán A, Mudarra AL, Alvarez E, Maseras F, Díaz-Requejo MM, Pérez PJ. Angew. Chem. Int. Ed. 2017; 56: 12842

24a Thornton AR, Blakey SB. J. Am. Chem. Soc. 2008; 130: 5020
24b Li C, Zhang L. Org. Lett. 2011; 13: 1738

25 Ram VJ, Sethi A, Nath M, Pratap R. The Chemistry of Heterocycles: Nomenclature and Chemistry of Three-to-Five-Membered Heterocycles. Elsevier; Amsterdam: 2019
26 Buchner E, Curtius T. Ber. Dtsch. Chem. Ges. 1885; 18: 2377
27 Rodríguez MR, Besora M, Molina F, Maseras F, Díaz-Requejo MM, Pérez PJ. J. Am. Chem. Soc. 2020; 142: 13062
28 Feast GC, Page LW, Robertson J. Chem. Commun. 2010; 46: 2835

29a Stoll AH, Blakey SB. J. Am. Chem. Soc. 2009; 132: 2108
29b Stoll AH, Blakey SB. Chem. Sci. 2011; 2: 112

30a Boralsky LA, Grigg RD, Marston D, Hershberger JC, Schomaker JM. Org. Lett. 2011; 13: 1924
30b Adams CS, Boralsky LA, Guzei IA, Schomaker JM. J. Am. Chem. Soc. 2012; 134: 10807
30c Burke EG, Schomaker JM. Angew. Chem. Int. Ed. 2015; 54: 12097
30d Schmid SC, Guzei IA, Schomaker JM. Angew. Chem. Int. Ed. 2017; 56: 12229
30e Grigg RD, Schomaker JM, Timokhin V. Tetrahedron 2011; 67: 4318
30f Weatherly CD, Rigoli JW, Schomaker JM. Org. Lett. 2012; 14: 1704
30g Weatherly CD, Guzei IA, Schomaker JM. Eur. J. Org. Chem. 2013; 3667
30h Rigoli JW, Weatherly CD, Vo BT, Neale S, Meis AR, Schomaker JM. Org. Lett. 2013; 15: 290
30i Rigoli JW, Weatherly CD, Alderson JM, Vo BT, Schomaker JM. J. Am. Chem. Soc. 2013; 135: 17238
30j Eshon J, Nicastri KA, Schmid SC, Raskopf WT, Guzei IA, Fernández I, Schomaker JM. Nat. Commun. 2020; 11: 1273

31 Quast H, Risler W. Angew. Chem., Int. Ed. Engl. 1973; 12: 414

32a Bayliffe FH, Steven A, Ando K, Shipman M. Synlett 2015; 26: 1371
32b Bayliffe F. Ph.D. Thesis . University of Warwick; UK: 2013