Nickel-Catalyzed Stille Cross Coupling of C–O Electrophiles

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alky...

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Veröffentlicht in:ACS catalysis 2019-04, Vol.9 (4), p.3304-3310
Hauptverfasser: Russell, John E. A, Entz, Emily D, Joyce, Ian M, Neufeldt, Sharon R
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.9b00744