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Synlett 2023; 34(14): 1639-1654
DOI: 10.1055/s-0042-1751425
DOI: 10.1055/s-0042-1751425
account
Our Voyage from Catalytic Cross-Hydroalkenylation to Transfer-Dehydroaromatization of Cyclic π-Systems: Reactivity and Selectivity Changes Enabled by NHC-Ni and NHC-Pd Hydride Equivalents
We thank Guangdong Provincial Key Laboratory of Catalysis (2020B121201002), Southern University of Science and Technology (SUSTech) (Y01501808, Y01506014), and the National Natural Science Foundation of China (NSFC) (22071096) for financial support.
Abstract
N-Heterocyclic carbene ligated transition-metal catalysts often show interesting properties and reactivity as compared to conventional ligand systems. In (NHC)Ni and (NHC)Pd hydrides, a dramatic reactivity changed from cross-hydroalkenylation to transfer-dehydroaromatization was observed under optimized conditions. This account summarizes our recent efforts and stories behind this serendipitous discovery. The mechanistic studies revealed that the keys to divert the desired reactivity are the differences in the olefin insertion selectivity and the hydrometallated species reactivity.
Key words
hydroalkenylation - transfer-hydrogenation - dehydroaromatization - N-heterocyclic carbenes - nickel - palladiumPublication History
Received: 13 January 2023
Accepted after revision: 06 February 2023
Article published online:
13 March 2023
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