The preparation of C-aryl glucals via palladium-catalyzed cross-coupling methods

The C-aryl glucals 17 - 31 have been prepared by the palladium-catalyzed cross coupling of 1-tributylstannyl-3,4,6-tri-O-(tert-butyldimethylsilyl)- D -glucal ( 11 ) and aryl bromides. The major by-product in all of these reactions is the dimer 33 , the product of homocoupling of 11 . Alternatively,...

Full description

Saved in:
Bibliographic Details
Published inCanadian journal of chemistry Vol. 72; no. 5; pp. 1262 - 1272
Main Authors Friesen, Richard W, Loo, Richard W, Sturino, Claudio F
Format Journal Article
LanguageEnglish
Published Ottawa, Canada NRC Research Press 01.05.1994
Natl Research Council Canada
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
HALIDES
MOLECULAR-STRUCTURE
1-TRIBUTYLSTANNYL GLYCALS
CHAETIACANDIN
TIN REAGENTS
ORGANOTIN REAGENTS
PAPULACANDIN-B
OXIDATIVE ADDITION
SYNTHETIC ROUTE
ORGANIC ELECTROPHILES
Online AccessGet full text

Cover

More Information
Summary:The C-aryl glucals 17 - 31 have been prepared by the palladium-catalyzed cross coupling of 1-tributylstannyl-3,4,6-tri-O-(tert-butyldimethylsilyl)- D -glucal ( 11 ) and aryl bromides. The major by-product in all of these reactions is the dimer 33 , the product of homocoupling of 11 . Alternatively, the C-aryl glucals 34-40 can be obtained from the palladium-catalyzed coupling of 1-iodo-3,4,6-tri-O-(triisopropylsilyl)- D -glucal ( 16 ) and a variety of metalated aromatics, including ArZnCl, ArB(OH) 2 , and ArB(OMe) 2 . The advantages of the latter procedure include superior coupling yields under milder reaction conditions and the high yielding preparation of 16 directly from 3,4,6-tri-O-(triisopropylsilyl)- D -glucal ( 12 ) by a metalation-iodination sequence.
ISSN:0008-4042
1480-3291
DOI:10.1139/v94-160