Substituent Effect of Bis(pyridines)iodonium Complexes as Iodinating Reagents: Control of the Iodocyclization/Oxidation Process

Halogen bond: The choice of the iodonium complex of pyridines, either IPy2PF6 or I(coll)2PF6 (Py=pyridine; coll=2,4,6‐trimethylpyridine), was crucial for controlling the iodocyclization/oxidation sequence of α‐propargylic glycine derivatives. This reagent‐controlled system enabled switchable access...

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Bibliographic Details
Published inChemistry : a European journal Vol. 19; no. 16; pp. 4992 - 4996
Main Authors Okitsu, Takashi, Yumitate, Saki, Sato, Kana, In, Yasuko, Wada, Akimori
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 15.04.2013
WILEY‐VCH Verlag
Wiley
Wiley Subscription Services, Inc
Subjects
Bonding
Chemistry
Chemistry, Multidisciplinary
Cyclization
Derivatives
Glycine
Halogens
Indicators and Reagents
iodine
Iodine - chemistry
Molecular Structure
Oxidation
Oxidation-Reduction
Physical Sciences
Pyridines
Pyridines - chemistry
Pyrroles
Science & Technology
substituent effects
synthetic methods
ELECTROPHILIC CYCLIZATION
MOLECULAR-IODINE
INTRAMOLECULAR ARYLATION
TERMINAL ACETYLENES
oxidation
ETHOXYETHYL ETHERS
ALKYNES
cyclization
INDENE DERIVATIVES
REACTION CASCADES
iodine
STEREOSELECTIVE-SYNTHESIS
substituent effects
OXIDATIVE AROMATIZATION
synthetic methods
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Summary:Halogen bond: The choice of the iodonium complex of pyridines, either IPy2PF6 or I(coll)2PF6 (Py=pyridine; coll=2,4,6‐trimethylpyridine), was crucial for controlling the iodocyclization/oxidation sequence of α‐propargylic glycine derivatives. This reagent‐controlled system enabled switchable access to 2,3‐dihydropyrroles and pyrroles (see scheme).
Bibliography:MEXT
ArticleID:CHEM201204423
ark:/67375/WNG-BTVB9NRK-6
Society of Iodine Science
istex:DA70EBD9A6AA83A34DDDD5D781C897CB66838412
Young Scientists (B)
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201204423