title: Palladium-catalyzed cross-coupling reactions of 4a,8a-azaboranaphthalene.
abstract: A concise and effective three-step synthesis of 4a,8a-azaboranaphthalene (ABN) has been developed in gram scale. Electrophilic aromatic substitution reactions of ABN provide excellent functional-group-tolerant cross-coupling partners in various Pd-catalyzed cross-coupling reactions (e.g., Sonogashira, Suzuki-Miyaura, or Heck reaction). Photophysical, electrochemical, and DFT calculations all suggest a narrowed HOMO-LUMO gap with extended π-conjugation characters in the cross-coupled molecules. The ABN moiety as a new fluorophore has a distinct and selective fluorescence response toward Zn(II) and Cd(II) ions, demonstrating great potential for the ABN structural motif in fluorescent chemosensors.
authors.affiliation: Department of Chemistry, Key Laboratory of Yangtze River Water Environment (Ministry of Education), Tongji University , 1239 Siping Road, Yangpu District, Shanghai 210092, People's Republic of China.
authors.forename: Feiye
authors.initials: F
authors.lastname: Sun
authors.forename: Lily
authors.initials: L
authors.lastname: Lv
authors.forename: Min
authors.initials: M
authors.lastname: Huang
authors.forename: Zhaohui
authors.initials: Z
authors.lastname: Zhou
authors.forename: Xiangdong
authors.initials: X
authors.lastname: Fang