Selection of boron reagents for Suzuki-Miyaura coupling

Selection of boron reagents for Suzuki-Miyaura coupling


Chem. Soc. Rev.
, 2014, Advance Article
DOI: 10.1039/C3CS60197H, Review Article

Alastair J. J. Lennox, Guy C. Lloyd-Jones
School of Chemistry, University of Edinburgh, West Mains Road, Edinburgh, EH9 3JJ, UK
This review analyses the general physical and chemical properties of the seven main classes of boron reagent that have been employed for SM coupling
Suzuki–Miyaura (SM) cross-coupling is arguably the most widely-applied transition metal catalysed carbon–carbon bond forming reaction to date. Its success originates from a combination of exceptionally mild and functional group tolerant reaction conditions, with a relatively stable, readily prepared and generally environmentally benign organoboron reagent. A variety of such reagents have been developed for the process, with properties that have been tailored for application under specific SM coupling conditions. This review analyses the seven main classes of boron reagent that have been developed. The general physical and chemical properties of each class of reagent are evaluated with special emphasis on the currently understood mechanisms of transmetalation. The methods to prepare each reagent are outlined, followed by example applications in SM coupling.

Three-Bond Breaking of Cyclic Anhydrides: Easy Access to Polyfunctionalized Naphthalenes and Phenanthrenes

School of Chemistry, College of Science, University of Tehran, 14155-6455 Tehran, Iran
Org. Lett., Article ASAP
Publication Date (Web): July 25, 2013 (Letter)
DOI: 10.1021/ol401318v

Benzannulation of phthalic anhydrides with alkynes to polyfunctionalized naphthalenes and phenanthrenes was confirmed to be straightforward using a palladium catalytic system. Sequential liberation of CO2 and CO occurred via oxidative decomposition of anhydride. In the case of 1,8-naphthalenedicarboxylic anhydrides, both aryls were encompassed in the annulation reaction to afford acenaphthylenes.