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21.1.4.1.3.2 Variation 2: With 3-Chloroperoxybenzoic Acid

DOI: 10.1055/sos-SD-021-00092

Cook, G. R.Science of Synthesis, (200521113.

Oxidation of aldimines 8 to N,N-disubstituted formamides 9 is best carried out using 3-chloroperoxybenzoic acid as the oxidant (Scheme 4).[‌6‌] Both yield and substrate scope are improved compared to the sodium perborate method (Section 21.1.4.1.3.1). In some cases, hydride migration competes with aryl migration to afford the N-substituted amide derivative 10.

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Meeeeeeeeee 8

Me8 Me8 Meeee (%) Mee
8 88
Me Me 88 8 [‌8‌]
8-Mee Me 88 8 [‌8‌]
8-MeMM8M8 Me 88 8 [‌8‌]
Me 8-MeM8M8 88 8 [‌8‌]
8-MeM8M8 Me 88 8 [‌8‌]
Me 8-MeMM8M8 88 88 [‌8‌]
8-MeMM8M8 8-MeMM8M8 88 88 [‌8‌]

Meeeeeeeeeee Meeeeeeee

Meeeeeeeeeeeeeeee (8, Me8=Me8=Me); Meeeeee Meeeeeeee:[‌8‌]

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