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DOI: 10.1055/sos-SD-024-01010

Witulski, B.; Alayrac, C.Science of Synthesis, (2006241009.

A general route to N,N-bis(trimethylsilyl)alky-1-yn-1-amines 13 is based upon the reactions of lithium acetylides 11 with O-(2,4,6-trimethylbenzenesulfonyl)-N,N-bis(trimethylsilyl)hydroxylamine (12) (Scheme 3).[‌28‌] By contrast, the electrophilic amination of the acetylides 11 cannot be performed with O-methanesulfonyl- or with O-diphenylphosphinyl-N,N-dimethylhydroxylamine. However, such reactions readily proceed with dilithium trialk-1-ynylcuprates 14, which are generated in situ from the corresponding lithium acetylides 11, to afford N,N-dimethylalk-1-yn-1-amines 15 (Scheme 3).[‌29‌]

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