Simple and reactive Ir(I) N-heterocyclic carbene complexes for alkyne activation

Mark R. D. Gatus, Indrek Pernik, Joshua A. Tompsett, Samantha C. Binding, Matthew B. Peterson, Barbara A. Messerle*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

Two simple unsymmetrical monometallic Ir(I) complexes with an N-heterocyclic carbene ligand and an analogous bimetallic Ir(I) complex were synthesised. These complexes were found to be extremely active catalysts for a range of C–X (X = N or O) and Si–N bond forming reactions involving alkyne and imine activation for dihydroalkoxylation, hydroamination and hydrosilylation reactions. These catalysts exhibited reaction rates far exceeding those of other Rh(I) and Ir(I) complexes previously reported. In addition, a small change to the ligand design (phenyl vs. mesityl) substantially affected both the reactivity and product selectivity of the catalyst. The Ir(I) complex bearing a mesitylene wingtip provided unprecedented regioselectivity in the dihydroalkoxylation reaction and a new kinetic product from the typical hydrosilylation protocol of 2-benyzlpyrroline to produce an N-silylaminoalkene. Our mechanistic studies indicated that this transformation proceeded via a dehydrogenative coupling mechanism.

Original languageEnglish
Pages (from-to)4333-4340
Number of pages8
JournalDalton Transactions
Volume48
Issue number13
DOIs
Publication statusPublished - 7 Apr 2019

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