Pyridine-4-thiol and Amphoteric Analogs: Novel Protection of Aryl Bromides in Strong Alkali

The use of pyridine‐4‐thiol (PT) to preserve certain aryl bromides in strong alkali is reported (Scheme 1). The presence of this additive or of some of its amphoteric analogs such as 3‐hydroxypyridin‐4(1H)‐ones suppresses the replacement of the Br‐substituent by hydroxide and alkoxide ions. A mechan...

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Bibliographic Details
Published inHelvetica chimica acta Vol. 91; no. 11; pp. 2062 - 2068
Main Authors Chen, Wei-Min, Cheng, Chao, Li, Bing-Zhou, Ho, Tse-Lok, Cai, Zhao-Shuo, Wang, Yuqiang, Sun, Ping-Hua
Format Journal Article
LanguageEnglish
Published Zürich WILEY-VCH Verlag 01.11.2008
WILEY‐VCH Verlag
Subjects
Amphoteric
Aryl bromide
Nucleophilic aromatic substitution
Protecting groups
Pyridine-4-thiol
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Summary:The use of pyridine‐4‐thiol (PT) to preserve certain aryl bromides in strong alkali is reported (Scheme 1). The presence of this additive or of some of its amphoteric analogs such as 3‐hydroxypyridin‐4(1H)‐ones suppresses the replacement of the Br‐substituent by hydroxide and alkoxide ions. A mechanistic interpretation of the effect is proposed.
Bibliography:ArticleID:HLCA200890219
istex:EAA8F4B369824714BDFB8A0D0F43D3FFB863944E
ark:/67375/WNG-QZLL3LRG-8
On leave from National Chiao Tung University, Hsinchu, Taiwan.
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.200890219