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

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

• 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