Ligand and counteranion enabled regiodivergent C–H bond functionalization of naphthols with α-aryl-α-diazoesters† †Electronic supplementary information (ESI) available: Data for new compounds, experimental procedures and theoretical studies on mechanisms. CCDC 1822536–1822538, 1884847. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c9sc01657k

• Published in: Chemical science (Cambridge) Vol. 10; no. 26; pp. 6553 - 6559
• Main Authors: Yu, Zhunzhun, Li, Yongfeng, Zhang, Peichao, Liu, Lu, Zhang, Junliang
• Format: Journal Article
• Language: English
• Published: Royal Society of Chemistry 27-05-2019
• Subjects: Chemistry
• ISSN: 2041-6520; 2041-6539
• DOI: 10.1039/c9sc01657k

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.
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 protocol potentially provides a novel design for C–H bond functionalization.