Nickel-Catalyzed Stille Cross Coupling of C-O Electrophiles

Authors

John E. A. Russell, Emily D. Entz, Ian M. Joyce, Sharon R. Neufeldt

Publication

ACS Catalysis

Abstract

Aryl sulfamates, tosylates, and mesylates undergo efficient Ni-catalyzed cross coupling with diverse organostannanes in the presence of relatively unhindered alkylphosphine ligands and KF. The coupling is valuable for difficult bond constructions, such as aryl—heteroaryl, aryl—alkenyl, and aryl—alkynyl, using nontriflate phenol derivatives. A combination of experimental and computational studies implicates an unusual mechanism for transmetalation involving an 8-centered cyclic transition state. This reaction is inhibited by chloride sources due to slow transmetalation of organostannanes at a Ni(II)—chloride intermediate. These studies help to explain why prior efforts to achieve Ni-catalyzed Stille coupling of phenol derivatives were unsuccessful.

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