Abstract
B(C6F5)3is demonstrated to be an active catalyst forN-alkylation reactions of amine substrates with aryl esters.
Highlights
PaperScheme 1 Amine synthesis catalyzed by triarylboranes
Unlike the frustrated Lewis pair (FLP) reductive amination approach, these reactions occur at lower temperatures and do not require the use of hydrogen gas or silane reductants
A simple facile metal-free reaction methodology has been demonstrated for the construction of C–N bond through N-alkylation using catalytic amounts of B(C6F5)[3]
Summary
PaperScheme 1 Amine synthesis catalyzed by triarylboranes. A) Previous work on the use of triarylboranes in reductive amination. Addition of 10 mol% B(C6F5)[3] led to C–N bond formation with elimination of p-fluorobenzoic acid to generate the N-alkylated product 3a in excellent isolated yields of 92% after 16 h at 80 °C. The Lewis/Brønsted acid activates the ester generating a carbenium species that is subsequently trapped by the amine nucleophile.
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