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Metal-free gem selective Dimerization of Terminal Alkynes cata-lyzed by a Pyridonate Borane complex

Abstract

A metal free gem selective dimerization of terminal alkynes catalyzed by a pyridonate borane complex is described. Each individual step of the catalytic cycle was verified experimentally and a protocol for a catalytic reaction was developed. The mechanism of the reaction was further investigated by DFT and DLPNO-CCSD(T) computations. The catalytic transformation commences with C–H cleavage by a boroxypyridne that displays frustrated Lewis pair reactivity. The pyridone borane complex that forms upon C-H cleavage dissociates into a pyridone and an alkynylborane. An unprecedented 1,2-carboration and a protodeborylation effected by the pyridone yield the 1,3-enyne and complete the catalytic cycle. The change in the coordination mode of the boroxypyridine upon C–H cleavage, described by the term boron-ligand cooperation, enables the dissociation of the formed pyridone borane complex and the 1,2-carboration and is thus vital for the catalytic reaction.

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Publication details

The article was received on 02 Feb 2019, accepted on 15 Apr 2019 and first published on 16 Apr 2019


Article type: Paper
DOI: 10.1039/C9CY00253G
Citation: Catal. Sci. Technol., 2019, Accepted Manuscript

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    Metal-free gem selective Dimerization of Terminal Alkynes cata-lyzed by a Pyridonate Borane complex

    M. Hasenbeck, T. Müller and U. Gellrich, Catal. Sci. Technol., 2019, Accepted Manuscript , DOI: 10.1039/C9CY00253G

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