Organic Letters 2012-08-03

Synthesis of aryl ethers via a sulfonyl transfer reaction.

Neal W Sach, Daniel T Richter, Stephan Cripps, Michelle Tran-Dubé, Huichun Zhu, Buwen Huang, Jean Cui, Scott C Sutton

Index: Org. Lett. 14(15) , 3886-9, (2012)

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Abstract

A general synthesis of aryl ethers from primary and secondary alcohols and aryl mesylates is presented. The reaction proceeds via a sulfonyl-transfer mechanism. In this paper, we compare the sulfonyl transfer reaction to Mitsunobu ether formation. The reaction can be employed in a multistep synthesis where the aryl mesylate is used as a phenol protecting group and then as an activating group for ether formation. This protecting/activating group strategy is demonstrated using raloxifene as the target.