Synthesis, Structure, and Reactivity of Anionic sp(2)-sp(3) Diboron   Compounds: Readily Accessible Boryl Nucleophiles

doi:10.1002/chem.201500235

CORC > 北京大学 > 化学与分子工程学院

	Synthesis, Structure, and Reactivity of Anionic sp(2)-sp(3) Diboron Compounds: Readily Accessible Boryl Nucleophiles
	Pietsch, Sabrina ; Neeve, Emily C. ; Apperley, David C. ; Bertermann, Ruediger ; Mo, Fanyang ; Qiu, Di ; Cheung, Man Sing ; Dang, Li ; Wang, Jianbo ; Radius, Udo ; Lin, Zhenyang ; Kleeberg, Christian ; Marder, Todd B.
刊名	CHEMISTRY-A EUROPEAN JOURNAL
	2015
关键词	boron boronic acids cross-coupling Lewis bases metal-free borylation ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS BORON CONJUGATE ADDITION CROSS-COUPLING REACTIONS N-HETEROCYCLIC CARBENES CATALYZED BETA-BORATION METAL-FREE DIBORATION LEWIS-BASE ADDUCTS BOND FORMATION H BONDS B BOND
DOI	10.1002/chem.201500235
英文摘要	Lewis base adducts of tetra-alkoxy diboron compounds, in particular bis(pinacolato)diboron (B(2)pin(2)), have been proposed as the active source of nucleophilic boryl species in metal-free borylation reactions. We report the isolation and detailed structural characterization (by solid-state and solution NMR spectroscopy and X-ray crystallography) of a series of anionic adducts of B(2)pin(2) with hard Lewis bases, such as alkoxides and fluoride. The study was extended to alternative Lewis bases, such as acetate, and other diboron reagents. The B(sp(2))-B(sp(3)) adducts exhibit two distinct boron environments in the solid-state and solution NMR spectra, except for [(4-tBuC(6)H(4)O)B(2)pin(2)](-), which shows rapid site exchange in solution. DFT calculations were performed to analyze the stability of the adducts with respect to dissociation. Stoichiometric reaction of the isolated adducts with two representative series of organic electrophilesnamely, aryl halides and diazonium saltsdemonstrate the relative reactivities of the anionic diboron compounds as nucleophilic boryl anion sources.; Deutsche Forschungsgemeinschaft (DFG); Royal Society; Alexander von Humboldt Foundation; EPSRC; Royal Society of Chemistry; DFG [Ma4471/1-1]; Research Grants Council of Hong Kong [HKUST 603313]; SCI(E); EI; ARTICLE; chzlin@ust.hk; ch.kleeberg@tu-braunschweig.de; todd.marder@uni-wuerzburg.de; 19; 7082-7098; 21
语种	英语
内容类型	期刊论文
源URL	[http://ir.pku.edu.cn/handle/20.500.11897/420229]
专题	化学与分子工程学院
推荐引用方式 GB/T 7714	Pietsch, Sabrina,Neeve, Emily C.,Apperley, David C.,et al. Synthesis, Structure, and Reactivity of Anionic sp(2)-sp(3) Diboron Compounds: Readily Accessible Boryl Nucleophiles[J]. CHEMISTRY-A EUROPEAN JOURNAL,2015.
APA	Pietsch, Sabrina.,Neeve, Emily C..,Apperley, David C..,Bertermann, Ruediger.,Mo, Fanyang.,...&Marder, Todd B..(2015).Synthesis, Structure, and Reactivity of Anionic sp(2)-sp(3) Diboron Compounds: Readily Accessible Boryl Nucleophiles.CHEMISTRY-A EUROPEAN JOURNAL.
MLA	Pietsch, Sabrina,et al."Synthesis, Structure, and Reactivity of Anionic sp(2)-sp(3) Diboron Compounds: Readily Accessible Boryl Nucleophiles".CHEMISTRY-A EUROPEAN JOURNAL (2015).