Efficient synthesis of acylsilanes using morpholine amides

Christopher T. Clark; Benjamin C. Milgram; Karl A. Scheidt

doi:10.1021/ol0483854

Efficient synthesis of acylsilanes using morpholine amides

Christopher T. Clark, Benjamin C. Milgram, Karl A. Scheidt^*

^*Corresponding author for this work

Chemistry

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37 Scopus citations

Abstract

(Chemical Equation Presented) A general synthesis of acylsilanes from the corresponding morpholine amides and silyllithium species is described. The use of morpholine amides is economical and prevents over-addition by the silyl nucleophile. The procedure cleanly affords acylsilanes in good yields and circumvents the use of stoichiometric copper(I) cyanide typically employed to synthesize these compounds from acid chlorides.

Original language	English (US)
Pages (from-to)	3977-3980
Number of pages	4
Journal	Organic Letters
Volume	6
Issue number	22
DOIs	https://doi.org/10.1021/ol0483854
State	Published - Oct 28 2004

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol0483854

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abstract = "(Chemical Equation Presented) A general synthesis of acylsilanes from the corresponding morpholine amides and silyllithium species is described. The use of morpholine amides is economical and prevents over-addition by the silyl nucleophile. The procedure cleanly affords acylsilanes in good yields and circumvents the use of stoichiometric copper(I) cyanide typically employed to synthesize these compounds from acid chlorides.",

author = "Clark, {Christopher T.} and Milgram, {Benjamin C.} and Scheidt, {Karl A.}",

year = "2004",

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doi = "10.1021/ol0483854",

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AU - Milgram, Benjamin C.

AU - Scheidt, Karl A.

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N2 - (Chemical Equation Presented) A general synthesis of acylsilanes from the corresponding morpholine amides and silyllithium species is described. The use of morpholine amides is economical and prevents over-addition by the silyl nucleophile. The procedure cleanly affords acylsilanes in good yields and circumvents the use of stoichiometric copper(I) cyanide typically employed to synthesize these compounds from acid chlorides.

AB - (Chemical Equation Presented) A general synthesis of acylsilanes from the corresponding morpholine amides and silyllithium species is described. The use of morpholine amides is economical and prevents over-addition by the silyl nucleophile. The procedure cleanly affords acylsilanes in good yields and circumvents the use of stoichiometric copper(I) cyanide typically employed to synthesize these compounds from acid chlorides.

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Efficient synthesis of acylsilanes using morpholine amides

Abstract

ASJC Scopus subject areas

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