An efficient and practical tin free procedure for radical iodine atom-transfer reactions

Iodine atom-transfer is a non-reductive and very attractive way of performing radical reactions that is usually achieved in the presence of hexaalkyldistannanes. We report here an efficient procedure to run such reactions in the absence of ditin derivatives. The iodine atom transfers are performed v...

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 11; pp. 1598 - 1602
Main Authors Ollivier, C, Bark, T, Renaud, P
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 2000
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ACID
isomerization
ring closure
radical reactions
ALPHA-IODO ESTERS
TRANSFER CYCLIZATION REACTIONS
peroxides
REACTION MIXTURES
TRIETHYLBORANE
ORGANOTIN RESIDUES
REMOVAL
BONDS
iodine
ADDITIONS
AMIDES
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Summary:Iodine atom-transfer is a non-reductive and very attractive way of performing radical reactions that is usually achieved in the presence of hexaalkyldistannanes. We report here an efficient procedure to run such reactions in the absence of ditin derivatives. The iodine atom transfers are performed via thermal initiation with commercially available and cheap dilauroyl peroxide (DLP). Good yields for intra- and intermolecular addition to alkenes are obtained. One example of aromatic substitution for the synthesis of an indolone derivative using stoichiometric amount of DLP is also reported.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-2000-7603