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Gold Catalyzed Cyclizations: A Comparative Study Between ortho,ortho'-Substituted KITPHOS Monophosphines and their Biaryl Monophosphine Counterpart SPHOS
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Dr Simon Doherty
Hashmi ASK, Loos A, Doherty S, Knight JGK, Robson KJ, Rominger F
Advanced Synthesis & Catalysis
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Electrophilic gold(I) triflimide complexes of electron-rich
´-disubstituted KITPHOS monophosphines are efficient catalysts for intramolecular cycloisomerizations that afford phenols, 3-acylindenes and methylene oxazolines; comparative catalyst testing showed that these catalysts either competed with or outperformed that based on SPHOS. An electron-rich biaryl monophosphine containing a single
-OMe substituent, prepared by rhodium-catalyzed [2+2+2] cycloaddition between a 1-alkynyl(dicyclohexylphosphine) oxide and 1,7-octadiyne, also formed a highly efficient catalyst for the same transformations. Monitoring of comparative catalyst testing between the a KITPHOS-based gold(I) triflimide complex containing a coordinated tetrahydrothiophene and its counterpart coordinated solely by the triflimide anion revealed that the former is an order of magnitude less efficient than the latter, confirming that tetrahydrothiophene can be an effective catalyst inhibitor.
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