Wittig Reaction in Deep Eutectic Solvents: Expanding the DES Toolbox in Synthesis.

Autor: De Nardi F; Dipartimento di Chimica, Università di Torino, Via Pietro Giuria 7, I-10125, Torino, Italy., Gorreta G; Dipartimento di Chimica, Università di Torino, Via Pietro Giuria 7, I-10125, Torino, Italy., Meazzo C; Dipartimento di Chimica, Università di Torino, Via Pietro Giuria 7, I-10125, Torino, Italy., Parisotto S; Dipartimento di Chimica, Università di Torino, Via Pietro Giuria 7, I-10125, Torino, Italy., Blangetti M; Dipartimento di Chimica, Università di Torino, Via Pietro Giuria 7, I-10125, Torino, Italy., Prandi C; Dipartimento di Chimica, Università di Torino, Via Pietro Giuria 7, I-10125, Torino, Italy.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2024 Sep 05; Vol. 30 (50), pp. e202402090. Date of Electronic Publication: 2024 Aug 20.
DOI: 10.1002/chem.202402090
Abstrakt: Wittig reaction between substituted phosphonium salts and (hetero)aromatic and alkyl carbonyl compounds in Deep Eutectic Solvents has been developed under a scalable and friendly protocol. Highly efficient reactions were successfully run with a wide range of bases including organic (DBU, LiTMP, t-BuOK) and inorganic (NaOH, K 2 CO 3 ) ones in ChCl/Gly 1 : 2 (mol/mol) as solvent under mild conditions, at room temperature and under air. The proposed protocol was applied to a wide range of substrates, including (hetero)aromatic aldehydes with substituents as halogens (I, Br, Cl), EDG (alkoxy, methyl), EWG (NO 2 , CF 3 ) or reactive groups as CN, esters, and ketones. Vinylic, alkynyl and cycloalkyl, alicyclic and α,β-unsaturated aldehydes can also be used. Highly electrophilic ketones gave good yields. The diastereoselectivity of the reaction is in complete agreement with the E/Z ratio predictable under traditional conditions. We demonstrated that the protocol is scalable to 2 g (5 mmol) of phosphonium salt, furthermore the proposed workup protocol allows to remove TPPO without need of additional chromatographic purification.
(© 2024 The Author(s). Chemistry - A European Journal published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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