CAS 61078-14-6, Cat. No EN300-7422491
Reagent for methylenation of carbonyl compounds
1-Methyl-2-(methylsulfonyl)-1H-benzimidazole (MBI) is a reagent for the methylenation of aldehydes and ketones by the Julia-Kocienski reaction1,2. Many analogous methods exist, such as the Wittig reaction or the Tebbe, Petasis reagents. Advantages of MBI that it offers higher yields with bigger chances of success. Besides these, MBI usage has a simple procedure and easily separated coproducts1,2. For sensitive substrates, the reaction could be carried out in DME at low temperatures using NaHMDS as a base with the same effectiveness2. The reagent is a bench-stable solid that can be stored for prolonged periods1,2.
Synonyms: 1-methyl-2-(methylsulfonyl)-1H-benzimidazole (ACI); benzimidazole 1-methyl-2-(methylsulfonyl)- (6CI); 1-methyl-2-methylsulfonylbenzimidazole; 2-methanesulfonyl-1-methyl-1H-benzoimidazole; MBI
Selected publications
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Practical Methylenation Reaction for Aldehydes and Ketones Using New Julia-Type Reagents.
Ando K.; Kobayashi T.; Uchida N. Org Lett 2015, 17 (10), 2554–2557. DOI: 10.1021/acs.orglett.5b01049
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Methylenation for Aldehydes and Ketones Using 1-Methylbenzimidazol-2-Yl Methyl Sulfone.
Ando K.; Oguchi M.; Kobayashi T.; Asano H.; Uchida N. J Org Chem 2020, 85 (15), 9936–9943. DOI: 10.1021/acs.joc.0c01227