Author:
Friesen Richard W.,Loo Richard W.,Sturino Claudio F.
Abstract
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.
Publisher
Canadian Science Publishing
Subject
Organic Chemistry,General Chemistry,Catalysis
Cited by
66 articles.
订阅此论文施引文献
订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献