Atom‐Economic Catalytic Direct Substitution of N, O‐Acetals with Simple Ketones. Issue 30 (15th August 2017)

• Record Type: Journal Article
• Authors: Touati, Bahria; El Bouakher, Abderrahman; Azizi, Mohamed Salah; Taillier, Catherine; Ben Othman, Raja; Trabelsi‐Ayadi, Malika; Antoniotti, Sylvain; Duñach, Elisabet; Dalla, Vincent
• Is Part Of: European journal of organic chemistry. Issue 30(2017)
• Page Start: 4445
• Page End: 4460
• Publication Date: 2017-08-15
• Subjects: Amidoalkylation -- Tin -- Lewis acids -- N, O‐acetals -- Enols -- Ketones; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201700530
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : A general and powerful catalytic protocol for the direct amidoalkylation of simple enolizable ketones is described, with use of the Lewis superacid Sn(NTf2 )4 as a catalyst under thermal conditions. A complete and rational study directed towards the development of efficient conditions for the coupling of a wide range of reaction partner combinations, including the most recalcitrant ones, is presented. The synthetic potential of the reaction is demonstrated through the use of a large set of both carbonyl and N, O‐acetalic substrates, providing the corresponding amidoalkylated ketones in 49–99 % yield, by using very low catalyst loadings (≤ 1 mol‐%). Abstract : A powerful catalytic protocol for the direct amidoalkylation of simple enolizable ketones with use of Lewis superacid Sn(NTf2 )4 as a catalyst is described. Couplings of a large set of both carbonyl and N, O‐acetalic substrates (mostly the simplest OH‐hemiaminals) proceed with very low catalyst loadings (≤ 1 mol‐%) and provide the corresponding amidoalkylated ketones in high yields (up to 99 %).