Metal-Free Coupling of Saturated Heterocyclic Sulfonylhydrazones with Boronic Acids

The coupling of aromatic moieties with saturated heterocyclic partners is currently an area of significant interest for the pharmaceutical industry. Herein, we present a procedure for the metal-free coupling of 4-, 5-, and 6-membered saturated heterocyclic p-methoxyphenyl (PMP) sulfonylhydrazones wi...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 79; no. 1; pp. 328 - 338
Main Authors Allwood, Daniel M, Blakemore, David C, Brown, Alan D, Ley, Steven V
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.01.2014
Amer Chemical Soc
Subjects
Boronic Acids - chemistry
Catalysis
Chemistry
Chemistry, Organic
Heterocyclic Compounds - chemistry
Hydrazones - chemistry
Metals - chemistry
Molecular Structure
Physical Sciences
Science & Technology
Stereoisomerism
HALIDES
COMPLEX
CROSS-COUPLINGS
SECONDARY ALKYL BROMIDES
BUILDING-BLOCKS
ARYLATION
TOSYLHYDRAZONES
ARYL
GRIGNARD-REAGENTS
ARYLBORONIC ACIDS
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Summary:The coupling of aromatic moieties with saturated heterocyclic partners is currently an area of significant interest for the pharmaceutical industry. Herein, we present a procedure for the metal-free coupling of 4-, 5-, and 6-membered saturated heterocyclic p-methoxyphenyl (PMP) sulfonylhydrazones with aryl and heteroaromatic boronic acids. This procedure enables a simple, two-step synthesis of a range of functionalized sp2–sp3 linked bicyclic building blocks, including oxetanes, piperidines, and azetidines, from their parent ketones.
Bibliography:ObjectType-Article-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/jo402526z