Manganese-Catalyzed Synthesis of Imines from Primary Alcohols and (Hetero)Aromatic Amines

Daniel Raydan; Sofia Friães; Nuno Viduedo; A. Sofia Santos; Clara S. B. Gomes; Beatriz Royo; M. Manuel B. Marques

doi:10.1055/a-1828-1678

Synlett, Table of Contents

Synlett 2022; 33(13): 1290-1294
DOI: 10.1055/a-1828-1678

letter

Manganese-Catalyzed Synthesis of Imines from Primary Alcohols and (Hetero)Aromatic Amines

Authors

Daniel Raydan‡

^aLAQV-REQUIMTE, Departamento de Química, NOVA School of Science and Technology, Universidade Nova de Lisboa, Campus de Caparica, 2829-516 Caparica, Portugal

^bITQB NOVA, Instituto de Tecnologia Química e Biológica António Xavier, Universidade Nova de Lisboa, Av. da República, 2780-157 Oeiras, Portugal
Sofia Friães‡

^bITQB NOVA, Instituto de Tecnologia Química e Biológica António Xavier, Universidade Nova de Lisboa, Av. da República, 2780-157 Oeiras, Portugal
Nuno Viduedo

^aLAQV-REQUIMTE, Departamento de Química, NOVA School of Science and Technology, Universidade Nova de Lisboa, Campus de Caparica, 2829-516 Caparica, Portugal
A. Sofia Santos

^aLAQV-REQUIMTE, Departamento de Química, NOVA School of Science and Technology, Universidade Nova de Lisboa, Campus de Caparica, 2829-516 Caparica, Portugal
Clara S. B. Gomes

^aLAQV-REQUIMTE, Departamento de Química, NOVA School of Science and Technology, Universidade Nova de Lisboa, Campus de Caparica, 2829-516 Caparica, Portugal

^cUCIBIO – Applied Molecular Biosciences Unit, Department of Chemistry, School of Science and Technology NOVA University Lisbon, 2819-516 Caparica, Portugal

^dAssociate Laboratory i4HB - Institute for Health and Bioeconomy, School of Science and Technology, NOVA University Lisbon, 2819-516 Caparica, Portugal
Beatriz Royo∗

^bITQB NOVA, Instituto de Tecnologia Química e Biológica António Xavier, Universidade Nova de Lisboa, Av. da República, 2780-157 Oeiras, Portugal
M. Manuel B. Marques ∗

^aLAQV-REQUIMTE, Departamento de Química, NOVA School of Science and Technology, Universidade Nova de Lisboa, Campus de Caparica, 2829-516 Caparica, Portugal

Abstract

All articles of this category

Abstract

Herein, we describe the synthesis of a wide variety of imines through oxidative coupling of alcohols and aromatic amines catalyzed by Mn complexes bearing N^N triazole ligands. A wide variety of imines in excellent yields (up to 99%) have been prepared. Mn-based catalysts proved to be highly efficient and versatile, allowing for the first time the preparation of several imines containing N-based heterocycles.

Key words

manganese - catalysis - imines - (hetero)aromatic amines - alcohols

Full Text

References

References
1 Ejiah FN, Fasina TM, Familoni OB, Ogunsola FT. Adv. Biol. Chem. 2013; 3: 475
2 da Silva CM, da Silva DL, Modolo LV, Alves RB, de Resende MA, Martins CV. B, De Fátima Â. J. Adv. Res. 2011; 2: 1
3 Chai H, Yu K, Liu B, Tan W, Zhang G. Organometallics 2020; 39: 217
4 Jiang G, Chen J, Huang J.-S, Che C.-M. Org. Lett. 2009; 11: 4568
5 So M.-H, Liu Y, Ho C.-M, Che C.-M. Chem. Asian J. 2009; 4: 1551
6 Choi H, Doyle MP. Chem. Commun. 2007; 745
7 Wang J.-R, Fu Y, Zhang B.-B, Cui X, Liu L, Guo Q.-X. Tetrahedron Lett. 2006; 47: 8293
8 Samec JS. M, Éll AH, Bäckvall J.-E. Chem. Eur. J. 2005; 11: 2327
9 Patil RD, Adimurthy S. Asian J. Org. Chem. 2013; 2: 726
10 Alvaro G, Savoia D. Synlett 2002; 651
11 Wang L, Zhang Y, Liu L, Wang Y. J. Org. Chem. 2006; 71: 1284
12 Orr SA, Andrews PC, Blair VL. Chem. Eur. J. 2021; 27: 2569
13 Martin SF. Pure Appl. Chem. 2009; 81: 195
14 Eftekhari-Sis B, Zirak M. Chem. Rev. 2017; 117: 8326
15 Noisier AF. M, Brimble MA. Chem. Rev. 2014; 114: 8775
16 Layer RW. Chem. Rev. 1963; 63: 489
17 Sprung MA. Chem. Rev. 1940; 26: 297
18 Palacios F, Alonso C, Aparicio D, Rubiales G, de los Santos JM. Tetrahedron 2007; 63: 523
19 Biswas N, Das K, Sardar B, Srimani D. Dalton Trans. 2019; 48: 6501
20 Liu L, Zhang S, Fu X, Yan C.-H. Chem. Commun. 2011; 47: 10148
21 Lang X, Ji H, Chen C, Ma W, Zhao J. Angew. Chem. Int. Ed. 2011; 50: 3934
22 Patil RD, Adimurthy S. Adv. Synth. Catal. 2011; 353: 1695
23 Chu G, Li C. Org. Biomol. Chem. 2010; 8: 4716
24 Yuan QL, Zhou XT, Ji HB. Catal. Commun. 2010; 12: 202
25 Jiang L, Jin L, Tian H, Yuan X, Yu X, Xu Q. Chem. Commun. 2011; 47: 10833
26 Sithambaram S, Kumar R, Son Y.-C, Suib SL. J. Catal. 2008; 253: 269
27 Sun H, Su F.-Z, Ni J, Cao Y, He H.-Y, Fan K.-N. Angew. Chem. Int. Ed. 2009; 48: 4390
28 Kwon MS, Kim S, Park S, Bosco W, Chidrala RK, Park J. J. Org. Chem. 2009; 74: 2877
29 Kim JW, He J, Yamaguchi K, Mizuno N. Chem. Lett. 2009; 38: 920
30 Blackburn L, Taylor RJ. K. Org. Lett. 2001; 3: 1637
31 Dias PiresM. J, Poeira DL, Marques MM. B. Eur. J. Org. Chem. 2015; 7197
32 Gunanathan C, Milstein D. Chem. Rev. 2014; 114: 12024
33 Esteruelas MA, Honczek N, Oliván M, Oñate E, Valencia M. Organometallics 2011; 30: 2468
34 Mukherjee A, Nerush A, Leitus G, Shimon LJ. W, Ben David Y, Espinosa JalapaN. A, Milstein D. J. Am. Chem. Soc. 2016; 138: 4298
35 Mastalir M, Glatz M, Gorgas N, Stöger B, Pittenauer E, Allmaier G, Veiros LF, Kirchner K. Chem. Eur. J. 2016; 22: 12316
36 Fertig R, Irrgang T, Freitag F, Zander J, Kempe R. ACS Catal. 2018; 8: 8525
37 Das K, Mondal A, Pal D, Srivastava HK, Srimani D. Organometallics 2019; 38: 1815
38 Valyaev DA, Lavigne G, Lugan N. Coord. Chem. Rev. 2016; 308: 191
39 Carney JR, Dillon BR, Thomas SP. Eur. J. Org. Chem. 2016; 3912
40 Schlichter P, Werlé C. Synthesis 2022; 54: 517
41 Maji B, Barman M. Synthesis 2017; 49: 3377
42 Wang Y, Wang M, Li Y, Liu Q. Chem 2021; 7: 1180
43 Mukherjee A, Milstein D. ACS Catal. 2018; 8: 11435
44 Zhang G, Irrgang T, Schlagbauer M, Kempe R. Chem. Catal. 2021; 1: 681
45 Zhang G, Irrgang T, Dietel T, Kallmeier F, Kempe R. Angew. Chem. Int. Ed. 2018; 57: 9131
46 Deibl N, Kempe R. Angew. Chem. Int. Ed. 2017; 56: 1663
47 Kallmeier F, Dudziec B, Irrgang T, Kempe R. Angew. Chem. Int. Ed. 2017; 56: 7261
48 Lenis-Rojas OA, Carvalho B, Cabral R, Silva M, Friães S, Roma-Rodrigues C, Meireles MS. H, Gomes CS. B, Fernández JA. A, Vila SF, Rubiolo JA, Sanchez L, Baptista PV, Fernandes AR, Royo B. J. Biol. Inorg. Chem. 2022; 27: 49

Supplementary Material

Supporting Information (PDF)