Microwave-assisted synthesis of N-heterocyclic carbene precursors

Aidouni, Adila; Demonceau, Albert; Delaude, Lionel

doi:10.1055/s-2006-932455

Download

Article (Scientific journals)

Microwave-assisted synthesis of N-heterocyclic carbene precursors

Aidouni, Adila; Demonceau, Albert; Delaude, Lionel

2006 • In Synlett, (3), p. 493-495

Peer Reviewed verified by ORBi

Permalink
https://hdl.handle.net/2268/15416

DOI
10.1055/s-2006-932455

Files (1)Send to Details Statistics Bibliography Similar publications

Files

Full Text

A027.pdf

Publisher postprint (77.16 kB)

Download

All documents in ORBi are protected by a user license.

Send to

RIS BibTex APA Chicago Permalink X Linkedin

Details

Keywords :

amines; cyclizations; heterocycles; imidazolinium salts; ligands

Abstract :

[en] A very simple and efficient procedure is reported for the synthesis of 1,3-diarylimidazolinium chlorides by cyclization of N,N'-diarylethylenediamines dihydrochlorides with triethyl ortho-formate under microwave irradiation.

Disciplines :

Chemistry

Author, co-author :

Aidouni, Adila

Demonceau, Albert ; Université de Liège - ULiège > Chimie macromoléculaire et catalyse organique

Delaude, Lionel ; Université de Liège - ULiège > Chimie macromoléculaire et catalyse organique

Language :

English

Title :

Microwave-assisted synthesis of N-heterocyclic carbene precursors

Publication date :

2006

Journal title :

Synlett

ISSN :

0936-5214

eISSN :

1437-2096

Publisher :

Georg Thieme Verlag Kg, Stuttgart, Germany

Issue :

Pages :

493-495

Peer reviewed :

Peer Reviewed verified by ORBi

Available on ORBi :

since 26 June 2009

Statistics

Number of views

136 (2 by ULiège)

Number of downloads

26 (1 by ULiège)

More statistics

Scopus citations^®

Scopus citations^®
without self-citations

OpenCitations

OpenAlex citations

Bibliography

(a) Herrmann, W. A.; Köcher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2162.
(b) Arduengo, A. J. III Acc. Chem. Res. 1999, 32, 913.
Bourissou, D.; Guerret, O.; Gabbaï, F. P.; Bertrand, G. Chem. Rev. 2000, 100, 39.
(a) Herrmann, W. A.; Kohl, F. J.; Schwartz, J. In Synthetic Methods of Organometallic and Inorganic Chemistry, Vol. 9; Herrmann, W. A., Ed.; Thieme: Stuttgart, 2000, 84.
(b) Herrmann, W. A.; Weskamp, T.; Böhm, V. P. W. Adv. Organomet. Chem. 2001, 48, 1.
(c) Herrmann, W. A. Angew. Chem. Int. Ed. 2002, 41, 1290.
(a) Jafarpour, L.; Nolan, S. P. Adv. Organomet. Chem. 2001, 46, 181.
(b) Scott, N. M.; Nolan, S. P. Eur. J. Inorg. Chem. 2005, 1815.
(c) Dragutan, I.; Dragutan, V.; Demonceau, A. Platinum Met. Rev. 2005, 49, 123.
(d) Dragutan, I.; Dragutan, V.; Demonceau, A. Platinum Met. Rev. 2005, 49, 183.
(a) Nair, V.; Bindu, S.; Sreekumar, V. Angew. Chem. Int. Ed. 2004, 43, 5130.
(b) Enders, D.; Balensiefer, T. Acc. Chem. Res. 2004, 37, 534.
César, V.; Bellemin-Laponnaz, S.; Gade, L. H. Chem. Soc. Rev. 2004, 33, 619.
(a) Arduengo, A. J. III; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 113, 361.
(b) Arduengo, A. J. III; Rasika Dias, H. V.; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1992, 114, 5530.
(c) Arduengo, A. J. III; Goerlich, J. R.; Marshall, W. J. J. Am. Chem. Soc. 1995, 117, 11027.
See, for example: (a) Delaude, L.; Szypa, M.; Demonceau, A.; Noels, A. F. Adv. Synth. Catal. 2002, 344, 749.
(b) Grasa, G. A.; Viciu, M. S.; Huang, J.; Zhang, C.; Trudell, M. L.; Nolan, S. P. Organometallics 2002, 21, 2866.
(c) Nyce, G. W.; Glauser, T.; Connor, E. F.; Möck, A.; Waymouth, R. M.; Hedrick, J. L. J. Am. Chem. Soc. 2003, 125, 3046.
(a) Arduengo, A. J. III; Krafczyk, R.; Schmutzler, R.; Craig, H. A.; Goerlich, J. R.; Marshall, W. J.; Unverzagt, M. Tetrahedron 1999, 55, 14523.
(b) Van Veldhuizen, J. J.; Gillingham, D. G.; Garber, S. B.; Kataoka, O.; Hoveyda, A. H. J. Am. Chem. Soc. 2003, 125, 12502.
(c) Ma, Y.; Song, C.; Jiang, W.; Wu, Q.; Wang, Y.; Liu, X.; Andrus, M. B. Org. Lett. 2003, 5, 3317.
(d) Xu, G.; Gilbertson, S. R. Org. Lett. 2005, 7, 4605.
(a) Saba, S.; Brescia, A.-M.; Kaloustian, M. K. Tetrahedron Lett. 1991, 32, 5031.
(b) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168.
(c) Grasa, G. A.; Viciu, M. S.; Huang, J.; Nolan, S. P. J. Org. Chem. 2001, 66, 7729.
(d) Seiders, T. J.; Ward, D. W.; Grubbs, R. H. Org. Lett. 2001, 3, 3225.
(e) Kingsbury, J. S.; Hoveyda, A. H. J. Am. Chem. Soc. 2005, 127, 4510.
(a) Microwaves in Organic Synthesis; Loupy, A., Ed.; Wiley-VCH: Weinheim, 2002.
(b) Kappe, C. O. Angew. Chem. Int. Ed. 2004, 43, 6250.
(c) Kappe, C. O.; Stadler, A. Microwaves in Organic and Medicinal Chemistry, In Methods and Principles in Medicinal Chemistry, Vol. 25; Mannhold, R.; Kubinyl, H.; Folkers, G., Eds.; Wiley-VCH: Weinheim, 2005.
(a) Caddick, S. Tetrahedron 1995, 51, 10403.
(b) Lidström, P.; Tierny, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225.
(c) Hayes, B. L. Aldrichimica Acta 2004, 37, 66.
Xu, Y.; Guo, Q.-X. Heterocycles 2004, 63, 903.
(a) Usyatinsky, A. Y.; Khmelnitsky, Y. L. Tetrahedron Lett. 2000, 41, 5031.
(b) Balalaie, S.; Arabanian, A. Green Chem. 2000, 2, 274.
(c) Wolkenberg, S. E.; Winoski, D. D.; Leister, W. H.; Wang, Y.; Zhao, Z.; Lindsley, C. W. Org. Lett. 2004, 6, 1453.
Starikova, O. V.; Dolgushin, G. V.; Larina, L. I.; Komarova, T. N.; Lopyrev, V. A. ARKIVOC 2003, (xiii), 119.
Hayes, B. L. Microwave Synthesis: Chemistry at the Speed of Light; CEM Publishing: Matthews, NC, 2002, 29-74.
General Procedure for the Microwave-Assisted Synthesis of 1,3-Diarylimidazolinium Chlorides. A 10-mL glass vial equipped with a stirring bar was charged with a N,N′-diarylethylenediamine dihydrochloride (1 mmol) and triethyl orthoformate (1-2 mL). The vial was capped and irradiated 5 min at 145°C (monitored by IR sensor) in a CEM Discover instrument with a 50-W microwave power. No ramp and no simultaneous cooling were applied. After rapid air cooling by the unit, the reaction mixture was diluted with Et2O (3 mL) and filtered under vacuum. The precipitate was rinsed with a few milliliters of Et2O and dried under vacuum to afford pure 1,3-diarylimidazolinium chloride.
1H NMR (400 MHz, DMSO-d6): δ = 2.35 (s, 6 H, para-CH3), 4.55 ppm (s, 4 H, CH2), 7.35 (d, J = 4.0 Hz, 2 H, CHortho), 7.60 (d, J = 4.0 Hz, 2 H, CHmeta), 10.13 (s, 1 H, im-CH2). 13C NMR (100 MHz, DMSO-d6): δ = 20.5 (para-CH3), 48.3 (CH2), 118.4 (CH ortho), 130.0 (CHmeta), 133.8 (Cpara), 136.4 (Cipso), 151.1 (im-CH2).
Maj, A.; Delaude, L.; Demonceau, A.; Noels, A. F. manuscript in preparation.
Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953.
Scaled-up Preparation of 1,3-Dimesitylimidazolinium Chloride. A 20-mL glass vial equipped with a stirring bar was charged with N,N′- dimesitylethylenediamine dihydrochloride (7.39 g, 20 mmol) and triethyl orthoformate (15 mL). The vial was capped and irradiated 5 min at 145°C (monitored by IR sensor) in a Biotage Emrys Optimizer instrument with a 75-W microwave power. No ramp was applied. After rapid cooling in an ice bath, the reaction mixture was diluted with Et2O (20 mL) and filtered under vacuum. The precipitate was rinsed with Et2O (2 × 10 mL) and dried under vacuum to afford pure 1,3-dimesitylimidazolinium chloride (6.57 g, 97% yield).