一种新型的、化学选择性的和高效的微波辅助脱保护硅醚的方法，使用的是 Selectfluor。

A novel, chemoselective and efficient microwave-assisted deprotection of silyl ethers with selectfluor.

机构信息

Centre for Synthesis and Chemical Biology, School of Chemistry and Chemical Biology, UCD Conway Institute, University College Dublin, Belfield, Dublin 4, Ireland.

出版信息

J Org Chem. 2009 Mar 6;74(5):2179-82. doi: 10.1021/jo802494t.

DOI:10.1021/jo802494t

PMID:19199653

Abstract

A novel microwave-assisted, chemoselective and efficient method for the cleavage of silyl ethers (aliphatic and aromatic) catalyzed by Selectfluor is reported. A wide range of TBS-, TIPS-, and TBDPS-protected alkyl silyl ethers can be chemoselectively cleaved in high yield in the presence of aryl silyl ethers. The chemoselective deprotection of phenolic TBS ethers, and not the TIPS- or TBDPS-protected phenolic ethers, and the deprotection of silyl esters were also achieved under these reaction conditions. In addition, the transetherification and etherification of benzylic hydroxy groups in alcoholic solvents is observed.

摘要

本文报道了一种新型的微波辅助、选择性好且高效的由 Selectfluor 催化的硅醚（脂肪族和芳香族）裂解方法。在芳基硅醚存在下，各种 TBS-、TIPS-和 TBDPS 保护的烷基硅醚可以高收率地选择性裂解。在这些反应条件下，还可以实现酚性 TBS 醚的选择性脱保护（而不是 TIPS 或 TBDPS 保护的酚性醚），以及硅酯的脱保护。此外，还观察到醇溶剂中苄基羟基的转醚化和醚化反应。