The facile alkylation and iodination of imidazol(in)ium salts in the presence of cesium carbonate.

Azolium salts; Imidazol; Weak basis; Electronic, Optical and Magnetic Materials; Catalysis; Ceramics and Composites; Chemistry (all); Surfaces, Coatings and Films; Metals and Alloys; Materials Chemistry; General Chemistry

Abstract :

[en] The alkylation or iodination of imidazol(in)ium salts takes place readily in the presence of Cs2CO3. The procedure is very easy to implement and provides facile and straightforward access to a wealth of C2-substituted azolium salts. Furthermore, a C2α alkylation is also feasible, which extends the chemistry of NHCs and weak bases to their NHO analogues.

Disciplines :

Chemistry

Author, co-author :

Mazars, François ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie organométallique et catalyse homogène

Zaragoza, Guillermo; Unidade de Difracción de Raios X, RIAIDT, Universidade de Santiago de Compostela, Campus Vida, 15782 Santiago de Compostela, Spain

Delaude, Lionel ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie organométallique et catalyse homogène

Language :

English

Title :

The facile alkylation and iodination of imidazol(in)ium salts in the presence of cesium carbonate.

Publication date :

07 December 2023

Journal title :

Chemical Communications

ISSN :

1359-7345

eISSN :

1364-548X

Publisher :

Royal Society of Chemistry (RSC), England

Volume :

Issue :

Pages :

14528 - 14531

Peer reviewed :

Peer Reviewed verified by ORBi

Additional URL :

http://pubs.rsc.org/en/content/articlepdf/2023/CC/D3CC04971J

Available on ORBi :

since 08 January 2024

Statistics

Number of views

36 (1 by ULiège)

Number of downloads

0 (0 by ULiège)

More statistics

Scopus citations^®

Scopus citations^®
without self-citations

OpenAlex citations

Bibliography

For monographs, see: (a) N-Heterocyclic Carbenes: Effective Tools for Organometallic Synthesis, ed. S. P. Nolan, Wiley-VCH, Weinheim, 2014
(b) Huynh H. V., The Organometallic Chemistry of N-heterocyclic Carbenes, Wiley, Hoboken (NJ), 2017
(c) N-Heterocyclic Carbenes: From Laboratory Curiosities to Efficient Synthetic Tools, ed. S. Díez-González, RSC Catalysis Series, Royal Society of Chemistry, Cambridge, 2nd edn, 2017, vol. 27
(d) N-Heterocyclic Carbenes in Catalytic Organic Synthesis, Science of Synthesis, ed. S. P. Nolan and C. S. J. Cazin, Thieme, Stuttgart, 2017
(e) N-Heterocyclic Carbenes in Organocatalysis, ed. A. T. Biju, Wiley-VCH, Weinheim, 2019
Arduengo III A. J. Harlow R. L. Kline M. J. Am. Chem. Soc. 1991 113 361 363 10.1021/ja00001a054
Arduengo, III A. J. Krafczyk R. Schmutzler R. Craig H. A. Goerlich J. R. Marshall W. J. Unverzagt M. Tetrahedron 1999 55 14523 14534 10.1016/S0040-4020(99)00927-8
For a few selected examples, see: Collado A. Gómez-Suárez A. Martin A. R. Slawin A. M. Z. Nolan S. P. Chem. Commun. 2013 49 5541 5543 10.1039/C3CC43076F 23677147
Visbal R. Laguna A. Gimeno M. C. Chem. Commun. 2013 49 5642 5644 10.1039/C3CC42919A 23685678
Santoro O. Collado A. Slawin A. M. Z. Nolan S. P. Cazin C. S. J. Chem. Commun. 2013 49 10483 10485 10.1039/C3CC45488F 24087835
Savka R. Plenio H. Dalton Trans. 2015 44 891 893 10.1039/C4DT03449J 25437103
Gehrke S. Hollóczki O. Angew. Chem., Int. Ed. 2017 56 16395 16398 10.1002/anie.201708305 29072807
Rico del Cerro D. Mera-Adasme R. King A. W. T. Perea-Buceta J. E. Heikkinen S. Hase T. Sundholm D. Wähälä K. Angew. Chem., Int. Ed. 2018 57 11613 11617 10.1002/anie.201805016 29987916
Gehrke S. Reckien W. Palazzo I. Welton T. Hollóczki O. Eur. J. Org. Chem. 2019 504 511 10.1002/ejoc.201801050
Hollóczki O. Chem. - Eur. J. 2020 26 4885 4894 10.1002/chem.201903021 31797448
Tzouras N. V. Nahra F. Falivene L. Cavallo L. Saab M. Van Hecke K. Collado A. Collett C. J. Smith A. D. Cazin C. S. J. Nolan S. P. Chem. - Eur. J. 2020 26 4515 4519 10.1002/chem.202000564 32022329
Zaby P. Blasius J. Müller A. K. Nolan S. P. Hollóczki O. Chem. - Eur. J. 2023 29 e202203636 10.1002/chem.202203636 36655873
Nelson D. J. Eur. J. Inorg. Chem. 2015 2012 2027 10.1002/ejic.201500061
For recent reviews, see: Martynova E. A. Tzouras N. V. Pisanò G. Cazin C. S. J. Nolan S. P. Chem. Commun. 2021 57 3836 3856 10.1039/D0CC08149C 33871505
Scattolin T. Logvinov A. A. Tzouras N. V. Cazin C. S. J. Nolan S. P. Organometallics 2023 42 2692 2730 10.1021/acs.organomet.3c00299
Di Marco L. Hans M. Delaude L. Monbaliu J.-C. M. Chem. - Eur. J. 2016 22 4508 4514 10.1002/chem.201505135 26880372
Mazars F. Hrubaru M. Tumanov N. Wouters J. Delaude L. Eur. J. Org. Chem. 2021 2025 2033 10.1002/ejoc.202100274
Dong H. Gu F. Li M. Lin B. Si Z. Hou T. Yan F. Lee S.-T. Li Y. ChemPhysChem 2014 15 3006 3014 10.1002/cphc.201402262 25383401
Hugar K. M. Kostalik H. A. I. V. Coates G. W. J. Am. Chem. Soc. 2015 137 8730 8737 10.1021/jacs.5b02879 26062959
Wang B. Qin L. Mu T. Xue Z. Gao G. Chem. Rev. 2017 117 7113 7131 10.1021/acs.chemrev.6b00594 28240867
Schulz N. Sokkar P. Engelage E. Schindler S. Erdelyi M. Sanchez-Garcia E. Huber S. M. Chem. - Eur. J. 2018 24 3464 3473 10.1002/chem.201705032 29160593
Squitieri R. A. Fitzpatrick K. P. Jaworski A. A. Scheidt K. A. Chem. - Eur. J. 2019 25 10069 10073 10.1002/chem.201902298 31112630
Sutar R. L. Engelage E. Stoll R. Huber S. M. Angew. Chem., Int. Ed. 2020 59 6806 6810 10.1002/anie.201915931 32045504
Higgins E. M. Sherwood J. A. Lindsay A. G. Armstrong J. Massey R. S. Alder R. W. O'Donoghue A. C. Chem. Commun. 2011 47 1559 1561 10.1039/C0CC03367G 21116519
Hollóczki O. Nyulászi L. Org. Biomol. Chem. 2011 9 2634 2640 10.1039/C1OB00007A 21399837
Gruseck U. Heuschmann M. Chem. Ber. 1987 120 2053 2064 10.1002/cber.19871201217
Blümel M. Noy J.-M. Enders D. Stenzel M. H. Nguyen T. V. Org. Lett. 2016 18 2208 2211 10.1021/acs.orglett.6b00835 27115463
Wang Z. Zheng Y. Zheng Y. Xue X.-S. Ji P. J. Phys. Chem. A 2018 122 5750 5755 10.1021/acs.jpca.8b02265 29893562