C−H Activation and Palladium Migration within Biaryls under Heck Reaction Conditions
- 14 August 2002
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 4 (18), 3115-3118
- https://doi.org/10.1021/ol026426v
Abstract
[reaction: see text] Biaryl bromides such as 1 (R=NO(2), H, OMe) undergo the Heck reaction to give both the expected products 3 ("retention") as well as "crossover" products 4 derived from a migration of Pd and net transfer of reactivity from one aryl ring to the other. Under the conditions used, crossover is increasingly favored when electron-deficient arenes are involved. Crossover products derived from transfer onto the pyridine ring have also been observed.Keywords
This publication has 5 references indexed in Scilit:
- Synthesis of 9-Alkylidene-9H-fluorenes by a Novel, Palladium-Catalyzed Cascade Reaction of Aryl Halides and 1-Aryl-1-alkynesThe Journal of Organic Chemistry, 2001
- Directed Deprotonation−Transmetalation as a Route to Substituted PyridinesOrganic Letters, 2001
- Palladium in action: domino coupling and allylic substitution reactions for the efficient construction of complex organic moleculesJournal of Organometallic Chemistry, 1999
- Transition-metal-assisted asymmetric synthesis of amino acid analogs. A new synthesis of optically pure D- and L-pyridylalaninesThe Journal of Organic Chemistry, 1991
- Mechanisms of intramolecular activation of carbon-hydrogen bonds in transition-metal complexesChemical Reviews, 1990