What can be the best alternative for EDC, DMAP as catalyst for carboxylates? I want to skip DMAP actually.
Dear Haroon Rashid,
Triphenylphosphine and mainly its supported form. Aren't you dealing with a Mitsunobu reaction conditions ? Regards
Dear all,
the following links on RG are all on the subject of Steglish reaction. Regards
https://www.researchgate.net/post/Steglich_Esterification_R_OH_RCOOH_RCOOR_with_EDC_DMAP_DCM/amp
https://www.researchgate.net/post/Whats_the_best_way_for_removing_extra_DCC_and_DMAP_in_an_esterification_reaction/amp
https://www.researchgate.net/post/Steglich_Esterification2/amp
https://www.researchgate.net/post/Steglich_esterification_solvents_DCC_DMAP_Coupling_What_are_the_implications_of_using_THF_as_the_solvent_in_this_reaction_instead_of_DCM_DMF/amp
I am working on an esterification reaction but I dont want DMAP here as catalyst as it is creating problem for me. So, I need some other procedure instead of steglich to activate carboxylate.
Dear Ong, Thank you for your suggestion. Actually, its act as base and I am dealing with carboxyl boronate, and boronate easily gets unstable due to this base. So, I need any catalyst which donot disturb boronates and just activate the carboxyl group of boronate with polyols, i am using, to make an ester.
There's an odd esterification method involving CBr4 that's fairly selective, but might work, depending on the structures of your substrates:
http://onlinelibrary.wiley.com/doi/10.1002/jccs.200300014/epdf
Also worth looking into are the many metal-based esterification catalysts (Ti, Zr, Sn, etc.) See attached review.
Mr. H. Rasheed,
Better you can also try with DBU, DABCO, Morpholine, Pyrrolidine, NMP.
In case if your moiety is not disturbed with acids, you can treat with thionyl chloride or oxalyl chloride to get converted into the corresponding acid chloride then treat with the other counterpart to get your desired product.
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