Selective Functionalization of Imidazoles Via an Iodine-copper Exchange Reaction
Overview
Authors
Affiliations
The reaction of protected 4,5-diiodoimidazoles with (PhMe2CCH2)2CuLi regioselectively provides 5-cuprated imidazoles, which readily react with various electrophiles furnishing functionalized imidazoles in good yields; remarkably, these resulting mono-iodoimidazoles undergo again an iodine-copper exchange reaction in the presence of sensitive functional groups, like an aldehyde or a ketone.
Nickel-catalyzed reductive conjugate addition to enones via allylnickel intermediates.
Shrestha R, Dorn S, Weix D J Am Chem Soc. 2012; 135(2):751-62.
PMID: 23270480 PMC: 3547151. DOI: 10.1021/ja309176h.
A flow-microreactor approach to protecting-group-free synthesis using organolithium compounds.
Kim H, Nagaki A, Yoshida J Nat Commun. 2011; 2:264.
PMID: 21468016 DOI: 10.1038/ncomms1264.
Total Syntheses of Naamidine G and 14-Methoxynaamidine G.
Koswatta P, Lovely C Tetrahedron Lett. 2010; 51(1):164-166.
PMID: 20161552 PMC: 2805157. DOI: 10.1016/j.tetlet.2009.10.117.
Total synthesis of (+/-)-calcaridine A and (+/-)-epi-calcaridine A.
Koswatta P, Sivappa R, Dias H, Lovely C Org Lett. 2008; 10(21):5055-8.
PMID: 18816134 PMC: 2650485. DOI: 10.1021/ol802018r.