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1.2.3.3.1 Trifluoromethanesulfonates

DOI: 10.1055/sos-SD-223-00066

Martin, A. R.Science of Synthesis: N-Heterocyclic Carbenes in Catalytic Organic Synthesis, (20161175.

Aryl trifluoromethanesulfonate (triflate) reagents can be used in Buchwald–Hartwig reactions when employing the palladium precatalysts 10 and 12 (L = IPr) (Scheme 18). The coupling is performed under reaction conditions analogous to those for aryl chloride reagents.[‌6‌,‌50‌] It requires only 1 mol% of precatalyst and the use of sodium tert-butoxide as the base. Electron-rich aryl trifluoromethanesulfonates are easily coupled to primary or secondary alkylamines and N-methylaniline. Unfortunately, no details about the steric hindrance or functional-group tolerance are available.

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References


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