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Synlett 2010(6): 841-851  
DOI: 10.1055/s-0029-1219531
ACCOUNT
© Georg Thieme Verlag Stuttgart ˙ New York

New Reagents for the Synthesis of Arylmethyl Ethers and Esters

Philip A. Albiniaka, Gregory B. Dudley*b
a Department of Chemistry, Ball State University, Muncie, IN 47306-0445, USA
b Department of Chemistry and Biochemistry, Florida State University, Tallahassee, FL 32306-4390, USA
Fax: +1(850) 644-8281; e-Mail: gdudley@chem.fsu.edu;
Further Information

Publication History

Received 6 November 2009
Publication Date:
18 February 2010 (online)

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Abstract

This Account chronicles efforts leading up to the development of new arylmethyl transfer (benzylation) reagents for protecting oxygen functional groups under relatively mild and neutral conditions. It begins with an investigation of organosiletanes as surrogate hydroxyl groups, which inspired siletane-functionalized benzyl ethers and forced us to confront the difficulties associated with the synthesis of benzyl ethers. The end result is a new series of neutral oxypyridinium salts for the benzylation of various nucleophilic functional groups under mild conditions.

1 Introduction

2 Tamao-type Oxidation of Strained Organosiletanes

3 p-Siletanylbenzyl (PSB) Protecting Groups

4 2-Benzyloxy-1-methylpyridinium Triflate

5 Friedel-Crafts Reactions and Mechanistic Insights

6 Benzyl Ester Formation

7 Substituted Benzyl Transfer Reagents

8 Conclusions and Outlook

Key words

siletanes - benzyl - PMB - PSB

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Aldrich catalog # 679674 2009/2010

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Aldrich catalog # 701440 2009/2010

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