Chan–Lam-Type C–N Cross-Coupling Reactions under Base- and Ligand-Free CuI-Zeolite Catalysis

Tony Garnier; Randa Sakly; Mathieu Danel; Stefan Chassaing; Patrick Pale

doi:10.1055/s-0036-1588652

Synthesis, Table of Contents

Synthesis 2017; 49(06): 1223-1230
DOI: 10.1055/s-0036-1588652

paper

Chan–Lam-Type C–N Cross-Coupling Reactions under Base- and Ligand-Free Cu^I-Zeolite Catalysis

Tony Garnier

^aInstitut des Technologies Avancées en sciences du Vivant (ITAV), Université de Toulouse, CNRS, UPS, 1 place Pierre Potier, 31106 Toulouse Cedex 1, France

,

Randa Sakly

^aInstitut des Technologies Avancées en sciences du Vivant (ITAV), Université de Toulouse, CNRS, UPS, 1 place Pierre Potier, 31106 Toulouse Cedex 1, France

^bLaboratoire de Chimie Organique Hétérocyclique, Produits Naturels et Réactivité (LCOHPNR), Faculté des Sciences de Monastir, Université de Monastir, Monastir, Tunisie

,

Mathieu Danel

^aInstitut des Technologies Avancées en sciences du Vivant (ITAV), Université de Toulouse, CNRS, UPS, 1 place Pierre Potier, 31106 Toulouse Cedex 1, France

,

Stefan Chassaing*

^aInstitut des Technologies Avancées en sciences du Vivant (ITAV), Université de Toulouse, CNRS, UPS, 1 place Pierre Potier, 31106 Toulouse Cedex 1, France

,

Patrick Pale*

^cLaboratoire de Synthèse, Réactivité Organique et Catalyse (LASYROC), Institut de Chimie, CNRS-UMR7177, Université de Strasbourg, 4 rue Blaise Pascal, 67070 Strasbourg, France Email: stefan.chassaing@itav.fr Email: ppale@unistra.fr

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Dedicated to the memory of Prof. J. F. Normant, a brilliant scientist and a wonderful person, and in recognition of his outstanding achievements in organometallic chemistry.

Abstract

Various representative copper(I)-exchanged zeolites were investigated for their catalytic potential in Chan–Lam cross-coupling reactions. Cu^I-USY appeared as the best catalyst and proved to efficiently promote C–N cross-coupling processes under attractive, simple, and practical conditions, namely refluxing in methanol under air and without any base.

Key words

copper - zeolites - heterogeneous catalysis - cross-coupling - Chan–Lam reaction - C–N bond formation

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References

References

1a Glaser C. Ber. Dtsch. Chem. Ges. 1869; 2: 422
1b Glaser C. Justus Liebigs Ann. Chem. 1870; 154: 137

2 Meerwein H, Buchner E, van Emster K. J. Prakt. Chem. 1939; 152: 237

3a Chodkiewicz W, Cadiot P. C. R. Hebd. Seances Acad. Sci. 1955; 241: 1055
3b Chodkiewicz W. Ann. Chim. (Paris) 1957; 2: 819

For the first examples, see:

4a Normant JF, Bourgain M. Tetrahedron Lett. 1971; 27: 2583

For reviews, see:

4b Normant JF. Synthesis 1972; 63
4c Normant JF, Alexakis A. Synthesis 1981; 841

5a Rappoport Z, Marek I. The Chemistry of Organocopper Compounds . Rappoport Z, Marek I. Wiley; Chichester: 2009
5b Krause N. Modern Organocopper Chemistry . Wiley-VCH; Weinheim: 2002

6a Ullmann F, Lehner A. Ber. Dtsch. Chem. Ges. 1904; 37: 853
6b Ullmann F, Sponagel P. Ber. Dtsch. Chem. Ges. 1905; 38: 2211

For reviews, see:

7a Beletskaya IP, Cheprakov AV. Coord. Chem. Rev. 2004; 248: 2337
7b Frlan R, Kikelj D. Synthesis 2006; 2271
7c Evano G, Blanchard N, Toumi M. Chem. Rev. 2008; 108: 3054
7d Monnier F, Taillefer M. Angew. Chem. Int. Ed. 2009; 48: 6954
7e Fischer C, Koenig B. Beilstein J. Org. Chem. 2011; 7: 59
7f Evano G, Theunissen C, Pradal A. Nat. Prod. Rep. 2013; 30: 1467
7g Sambiagio C, Marsden SP, Blacker AP, McGowan PC. Chem. Soc. Rev. 2014; 43: 3525

8 Chan DM. T, Monaco KL, Wang R.-P, Winters MP. Tetrahedron Lett. 1998; 39: 2933
9 Lam PY. S, Clark CG, Saubern S, Adams J, Winters MP, Chan DM. T, Combs A. Tetrahedron Lett. 1998; 39: 2941
10 Evans DA, Katz JL, West TR. Tetrahedron Lett. 1998; 39: 2937

11a Qiao JX, Lam PY. S. Synthesis 2011; 829
11b Rao KS, Wu T.-S. Tetrahedron 2012; 68: 7735

12a Collman JP, Zhong M. Org. Lett. 2000; 2: 1233
12b Lan J.-B, Chen L, Yu X.-Q, You J.-S, Xie R.-G. Chem. Commun. 2004; 188
12c Uemura T, Chatani N. J. Org. Chem. 2005; 70: 8631
12d Moessner C, Bolm C. Org. Lett. 2005; 7: 2667
12e Wentzel MT, Hewgley JB, Kamble RM, Wall PD, Kozlowski MC. Adv. Synth. Catal. 2009; 351: 931

13 Barboro P, Liguori F. Heterogenized Homogeneous Catalysts for Fine Chemicals Production. Springer; Dordrecht: 2010
14 Kantam ML, Venkanna GT, Sridhar C, Sreedhar B, Choudary BM. J. Org. Chem. 2006; 71: 9522
15 Sreedhar B, Venkanna GT, Kumar KB. S, Balasubrahmanyam V. Synthesis 2008; 795
16 Azarifar D, Soleimanei F. RSC Adv. 2014; 4: 12119
17 Chassaing S, Beneteau V, Pale P. Catal. Sci. Technol. 2016; 6: 923

18a Chassaing S, Alix A, Boringari T, Sani Souna Sido A, Keller M, Kuhn P, Louis B, Sommer J, Pale P. Synthesis 2010; 1557
18b Chassaing S, Alix A, Olmos A, Keller M, Sommer J, Pale P. Z. Naturforsch., B 2010; 65b: 783

19a Chassaing S, Kumarraja M, Sani Souna Sido A, Pale P, Sommer J. Org. Lett. 2007; 9: 883
19b Chassaing S, Sani Souna Sido A, Alix A, Kumarraja M, Pale P, Sommer J. Chem. Eur. J. 2008; 14: 6713
19c Alix A, Chassaing S, Pale P, Sommer J. Tetrahedron 2008; 64: 8922
19d Bénéteau V, Olmos A, Boningari T, Sommer J, Pale P. Tetrahedron Lett. 2010; 51: 3673
19e Boringari T, Olmos A, Reddy BM, Sommer J, Pale P. Eur. J. Org. Chem. 2010; 6338
19f Keller M, Sani Souna Sido A, Pale P, Sommer J. Chem. Eur. J. 2009; 15: 2810
19g Patil MK, Keller M, Reddy BM, Pale P, Sommer J. Eur. J. Org. Chem. 2008; 4440
19h Kuhn P, Alix A, Kumarraja M, Louis B, Pale P, Sommer J. Eur. J. Org. Chem. 2009; 423
19i Kuhn P, Pale P, Sommer J, Louis B. J. Phys. Chem. C 2009; 113: 2903
19j Harkat H, Borghèse S, De Nigris M, Kiselev S, Bénéteau V, Pale P. Adv. Synth. Catal. 2014; 356: 3842
19k Magné V, Garnier T, Danel M, Pale P, Chassaing S. Org. Lett. 2015; 17: 4494

20 It has been shown that boroxine can participate in Chan–Lam–Evans coupling reactions. For more details, see ref. 10 and: Chan DM. T, Monaco KL, Li R, Bonne D, Clark CG, Lam PY. S. Tetrahedron Lett. 2003; 44: 3863

21a Derouane EG. J. Mol. Catal. A 1998; 134: 29
21b Sastre GA, Corma A. J. Mol. Catal. A 2009; 305: 3

22 Cundy DJ, Forsyth SA. Tetrahedron Lett. 1998; 39: 7979
23 Amatore C, Le Duc G, Jutand A. Chem. Eur. J. 2013; 19: 10082
24 Casitas A, King AE, Parella T, Costas M, Stahl SS, Ribas X. Chem. Sci. 2010; 1: 326

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