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What is the difference between mono- and biphosphine ligands? Revealing the chemoselectivity in Pd-catalysed carbenation of bromonaphthalene

ORGANIC CHEMISTRY FRONTIERS(2022)

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摘要
Ligand-controlled chemoselectivity is an important topic in organometallic chemistry. In this work, DFT calculations were used to reveal the chemoselectivity of a Pd-catalysed three-component dearomative carbenation of bromonaphthalene with diazo compounds and allylborates. When a monophosphine ligand was used, ligand exchange with a diazo compound was favored by the release of a phosphine ligand. Therefore, a three-component coupling reaction could occur. However, when a biphosphine ligand was used, ligand exchange between the phosphine and the diazo compounds was difficult. Therefore, the Suzuki-Miyaura coupling product was observed in this case, without the participation of the carbene moiety.
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关键词
biphosphine ligands,chemoselectivity,pd-catalysed
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