Practical Thiol Surrogates and Protective Groups for Arylthiols for Suzuki−Miyaura Conditions

We have developed practical thiol surrogates and arylthiol protective groups for the Suzuki−Miyaura reaction. 2-Ethylhexyl-3-mercaptopropionate and 4-(2‘-mercaptoethyl)pyridine were shown to be not only good thiol surrogates but also good protective groups for thiol. We have demonstrated toleration...

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Bibliographic Details
Published in:Journal of organic chemistry 2006-03, Vol.71 (5), p.2203-2206
Main Authors: Itoh, Takahiro, Mase, Toshiaki
Format: Article
Language:English
Subjects:
3-Mercaptopropionic Acid - analogs & derivatives
3-Mercaptopropionic Acid - chemical synthesis
3-Mercaptopropionic Acid - chemistry
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
Pyridines - chemical synthesis
Pyridines - chemistry
Sulfhydryl Compounds - chemical synthesis
Sulfhydryl Compounds - chemistry
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Summary:We have developed practical thiol surrogates and arylthiol protective groups for the Suzuki−Miyaura reaction. 2-Ethylhexyl-3-mercaptopropionate and 4-(2‘-mercaptoethyl)pyridine were shown to be not only good thiol surrogates but also good protective groups for thiol. We have demonstrated toleration of these protective groups under aqueous Suzuki−Miyaura conditions.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo052624z