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Simple Methodology for Heck Arylation at C-8 of Adenine Nucleosides

✍ Scribed by Pallavi Lagisetty; Li Zhang; Mahesh K. Lakshman

Publisher
John Wiley and Sons
Year
2008
Tongue
English
Weight
223 KB
Volume
350
Category
Article
ISSN
1615-4150

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✦ Synopsis

Abstract

A simple method for the arylation of 8‐vinyladenine nucleoside derivatives is reported. With a broad set of aryl iodides and bromides, the reaction is catalyzed by the simple combination palladium acetate/tris(o‐tolyl)phosphine/triethylamine [Pd(OAc)~2~/(o‐tol)~3~P/Et~3~N]. As expected, aryl chlorides are more difficult coupling partners but some undergo reactions with more exotic catalysts. Although trans‐olefins are the major products, minor amounts of cis‐isomers are detected in some cases, and a post‐arylation mechanism for their formation is proposed. Finally, by subtle catalyst modulation chemoselective N‐arylation of the nucleoside can be achieved in the presence of the vinyl moiety.

📜 SIMILAR VOLUMES

Corrigendum: Simple Methodology for Heck
Corrigendum: Simple Methodology for Heck Arylation at C-8 of Adenine Nucleosides
✍ Pallavi Lagisetty; Li Zhang; Mahesh K. Lakshman 📂 Article 📅 2011 🏛 John Wiley and Sons 🌐 English ⚖ 50 KB 👁 1 views

For the full paper by Pallavi Lagisetty, Li Zhang and Mahesh K. Lakshman, in Issue 4, 2008, pp 602–608 (DOI: 10.1002/adsc.200700418), the Supporting Information has been corrected to rectify errors in the HR‐MS analysis, such as the technique used for obtaining the data.

ChemInform Abstract: Simple Methodology
ChemInform Abstract: Simple Methodology for Heck Arylation at C-8 of Adenine Nucleosides.
✍ Pallavi Lagisetty; Li Zhang; Mahesh K. Lakshman 📂 Article 📅 2008 🏛 John Wiley and Sons ⚖ 44 KB 👁 1 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v