Synthesis of aryl ethers via a sulfonyl transfer reaction.
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.
Pfizer Global Research and Development, 10770 Science Center Drive, San Diego, California 92121, USA.
Neal W
NW
Sach
Daniel T
DT
Richter
Stephan
S
Cripps
Michelle
M
Tran-Dubé
Huichun
H
Zhu
Buwen
B
Huang
Jean
J
Cui
Scott C
SC
Sutton
D000438:Alcohols / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D010636:Phenols / Q000138:chemical synthesis; D020849:Raloxifene Hydrochloride / Q000138:chemical synthesis* / Q000737:chemistry; D013329:Structure-Activity Relationship
D000438:Alcohols; D004987:Ethers; D008698:Mesylates; D010636:Phenols; C045880:methanesulfonic acid; D020849:Raloxifene Hydrochloride