Trimethylsilyl bis (trifluoromethanesulfonyl) imide as a tolerant and environmentally benign Lewis acid catalyst of the Diels–Alder reaction

B Mathieu, L Ghosez

Index: Mathieu, Benoit; Ghosez, Leon Tetrahedron, 2002 , vol. 58, # 41 p. 8219 - 8226

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Citation Number: 96

Abstract

N-trimethylsilyl bis (trifluoromethanesulfonyl) imide (TMSNTf2) was readily prepared in situ by protodesilylation of trimethylsilane, allyl-or phenyltrimethylsilane with bis (trifluoromethylsulfonyl) imide. NMR studies showed that TMSNTf2 was much more effective than TMSOTf in complexing the carbonyl group of trans-methylcrotonate. As a result, TMSNTf2 was found to be superior to TMSOTf as a catalyst for the Diels–Alder reaction of ...