UNIGE document Scientific Article
previous document  unige:92434  next document
add to browser collection
Title

Palladium-Catalyzed Hydrohalogenation of 1,6-Enynes: Hydrogen Halide Salts and Alkyl Halides as Convenient HX Surrogates

Authors
Petrone, David A.
Ye, Juntao
Rodríguez, José F.
Lautens, Mark
Published in Journal of the American Chemical Society. 2017, vol. 139, no. 9, p. 3546-3557
Abstract Difficulties associated with handling H2 and CO in metal-catalyzed processes have led to the development of chemical surrogates to these species. Despite many successful examples using this strategy, the application of convenient hydrogen halide (HX) surrogates in catalysis has lagged behind considerably. We now report the use of ammonium halides as HX surrogates to accomplish a Pd-catalyzed hydrohalogenation of enynes. These safe and practical salts avoid many drawbacks associated with traditional HX sources including toxicity and corrosiveness. Experimental and computational studies support a reaction mechanism involving a crucial E-to-Z vinyl–Pd isomerization and a carbon–halogen bond-forming reductive elimination. Furthermore, rare examples of C(sp3)–Br and −Cl reductive elimination from Pd(II) as well as transfer hydroiodination using 1-iodobutane as an alternate HI surrogate are also presented.
Identifiers
Full text
Article (Published version) (2.6 MB) - document accessible for UNIGE members only Limited access to UNIGE
Structures
Research group Groupe Poblador Bahamonde
Citation
(ISO format)
PETRONE, David A. et al. Palladium-Catalyzed Hydrohalogenation of 1,6-Enynes: Hydrogen Halide Salts and Alkyl Halides as Convenient HX Surrogates. In: Journal of the American Chemical Society, 2017, vol. 139, n° 9, p. 3546-3557. doi: 10.1021/jacs.7b00482 https://archive-ouverte.unige.ch/unige:92434

405 hits

0 download

Update

Deposited on : 2017-03-08

Export document
Format :
Citation style :