Carbolithiation of S-alkenyl-N-aryl thiocarbamates: Carbanion arylation in a connective route to tertiary thiols

Daniele Castagnolo; Daniel J. Foley; Hatice Berber; Renzo Luisi; Jonathan Clayden

doi:10.1021/ol400570r

Carbolithiation of S-alkenyl-N-aryl thiocarbamates: Carbanion arylation in a connective route to tertiary thiols

Daniele Castagnolo, Daniel J. Foley, Hatice Berber, Renzo Luisi, Jonathan Clayden^*

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

20 Citations (Scopus)

Abstract

S-Alkenyl-N-arylthiocarbamates are formed from allylic alcohols by sigmatropic rearrangement and isomerization or C=C bond cleavage. They undergo carbolithiation with a range of organolithium reagents, generating benzyllithium intermediates in a stereospecific manner which may undergo N to C aryl migration to yield thiocarbamates with tertiary substituents. A simple base-promoted alcoholysis reveals a series of hindered tertiary thiols with branched carbon skeletons.

Original language	English
Pages (from-to)	2116-2119
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	9
Early online date	15 Apr 2013
DOIs	https://doi.org/10.1021/ol400570r
Publication status	Published - 3 May 2013

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abstract = "S-Alkenyl-N-arylthiocarbamates are formed from allylic alcohols by sigmatropic rearrangement and isomerization or C=C bond cleavage. They undergo carbolithiation with a range of organolithium reagents, generating benzyllithium intermediates in a stereospecific manner which may undergo N to C aryl migration to yield thiocarbamates with tertiary substituents. A simple base-promoted alcoholysis reveals a series of hindered tertiary thiols with branched carbon skeletons.",

author = "Daniele Castagnolo and Foley, {Daniel J.} and Hatice Berber and Renzo Luisi and Jonathan Clayden",

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T1 - Carbolithiation of S-alkenyl-N-aryl thiocarbamates

T2 - Carbanion arylation in a connective route to tertiary thiols

AU - Castagnolo, Daniele

AU - Foley, Daniel J.

AU - Berber, Hatice

AU - Luisi, Renzo

AU - Clayden, Jonathan

PY - 2013/5/3

Y1 - 2013/5/3

N2 - S-Alkenyl-N-arylthiocarbamates are formed from allylic alcohols by sigmatropic rearrangement and isomerization or C=C bond cleavage. They undergo carbolithiation with a range of organolithium reagents, generating benzyllithium intermediates in a stereospecific manner which may undergo N to C aryl migration to yield thiocarbamates with tertiary substituents. A simple base-promoted alcoholysis reveals a series of hindered tertiary thiols with branched carbon skeletons.

AB - S-Alkenyl-N-arylthiocarbamates are formed from allylic alcohols by sigmatropic rearrangement and isomerization or C=C bond cleavage. They undergo carbolithiation with a range of organolithium reagents, generating benzyllithium intermediates in a stereospecific manner which may undergo N to C aryl migration to yield thiocarbamates with tertiary substituents. A simple base-promoted alcoholysis reveals a series of hindered tertiary thiols with branched carbon skeletons.

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U2 - 10.1021/ol400570r

DO - 10.1021/ol400570r

M3 - Article (Academic Journal)

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JO - Organic Letters

JF - Organic Letters

IS - 9

ER -

Carbolithiation of S-alkenyl-N-aryl thiocarbamates: Carbanion arylation in a connective route to tertiary thiols

Abstract

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