Dehydroxylation of alcohols for nucleophilic substitution

The Ph 3 P/ICH 2 CH 2 I system-promoted dehydroxylative substitution of alcohols was achieved to construct C-O, C-N, C-S and C-X (X = Cl, Br, and I) bonds. Compared with the previous approaches such as the Appel reaction and Mitsunobu reaction, this protocol offers some practical advantages such as...

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Bibliographic Details
Published inChemical communications (Cambridge, England) Vol. 54; no. 51; pp. 734 - 737
Main Authors Chen, Jia, Lin, Jin-Hong, Xiao, Ji-Chang
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 21.06.2018
Royal Society of Chemistry
Subjects
Alcohol
Alcohols
amination
bromine
Chemistry
Chemistry, Multidisciplinary
chlorine
iodine
Lewis bases
Physical Sciences
Science & Technology
Substitution reactions
MICHAELIS-ARBUZOV REARRANGEMENT
MECHANISM
DIFLUOROCARBENE
WITTIG REACTION
DIETHYL AZODICARBOXYLATE
DEHYDRATION
MITSUNOBU REACTIONS
APPEL CONDITIONS
TRIPHENYLPHOSPHINE
PHASE S(N)2 REACTION
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Summary:The Ph 3 P/ICH 2 CH 2 I system-promoted dehydroxylative substitution of alcohols was achieved to construct C-O, C-N, C-S and C-X (X = Cl, Br, and I) bonds. Compared with the previous approaches such as the Appel reaction and Mitsunobu reaction, this protocol offers some practical advantages such as safe operation and a convenient amination process. The convenient dehydroxylative substitution of alcohols with various nucleophiles promoted by the Ph 3 P/ICH 2 CH 2 I system under mild conditions is described.
Bibliography:Electronic supplementary information (ESI) available. See DOI
10.1039/c8cc03856b
ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1359-7345
1364-548X
1364-548X
DOI:10.1039/c8cc03856b