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Ligand and counteranion enabled regiodivergent C-H bond functionalization of naphthols with ?-aryl-?-diazoesters.

ABSTRACT: Here, an unprecedented ligand and counteranion-controlled and site-selectivity switchable direct C-H bond functionalization of unprotected naphthols with ?-aryl-?-diazoesters was developed. In this transformation, site selectivities are realized by turning on/off the coordination between metal complexes and hydroxy groups. The preliminary mechanism revealed that the interaction between the hydroxy group and gold catalyst plays a key role in switching the site-selectivity of gold-carbene. This protocol potentially provides a novel design for C-H bond functionalization.

SUBMITTER: Yu Z

PROVIDER: S-EPMC6615435 | biostudies-literature | 2019 Jul

REPOSITORIES: biostudies-literature

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Ligand and counteranion enabled regiodivergent C-H bond functionalization of naphthols with α-aryl-α-diazoesters.

Yu Zhunzhun Z Li Yongfeng Y Zhang Peichao P Liu Lu L Zhang Junliang J

Chemical science 20190527 26

Here, an unprecedented ligand and counteranion-controlled and site-selectivity switchable direct C-H bond functionalization of unprotected naphthols with α-aryl-α-diazoesters was developed. In this transformation, site selectivities are realized by turning on/off the coordination between metal complexes and hydroxy groups. The preliminary mechanism revealed that the interaction between the hydroxy group and gold catalyst plays a key role in switching the site-selectivity of gold-carbene. This pr ...[more]

PMID: 31367307

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