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The Scope of Radical CC‐Coupling by the “Tin Method”
Author(s) -
Giese Bernd,
GonzálezGómez Juan Antonio,
Witzel Tom
Publication year - 1984
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198400691
Subject(s) - acrylonitrile , tributyltin hydride , chemistry , aldehyde , reagent , ketone , catalysis , tributyltin , alkyl , tin , organic chemistry , hydride , medicinal chemistry , hydrogen , polymer , copolymer
The widely useful tributyltin hydride as catalyst (in the presence of NaBH 4 ) effects the radical chain lengthening of alkyl iodides with acrylonitrile or alkenes which contain, e.g. ketone aldehyde, ester or phenyl substituents. As reagent, tributyltin hydride enables a convenient synthesis of C ‐branched deoxy sugars. A sugar such as 1 , Y OH , is converted into a xanthogenate or thiourethane, which e.g., reacts with acrylonitrile to give 2 , R CH 2 CH 2 CN.
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