Iron-Catalyzed Cadiot-Chodkiewicz Coupling with High Selectivity in Water under Air
Yi-An Liao1, Wen-Sheng Peng1, Ling-Jun Liu1
1Institute of Organic and Polymeric Materials, National Taipei University of Technology, Taipei 10608, Taiwan.
Abstract:
An iron-based catalytic system was developed for the cross-coupling of 1-bromoalkynes with terminal alkynes to selectively generate unsymmetrical 1,3-butadiynes in water under air. It was found that a combination of 1-bromoalkynes derived from less acidic terminal alkynes with more acidic counterparts would greatly enhance yields and selectivity for unsymmetrical 1,3-butadiynes. The reaction was also applicable for the synthesis of unsymmetrical 1,3,5-hexatriynes through coupling of 1-bromoalkynes and trimethylsilyl-protected 1,3-butadiynes in a one-pot manner.
Related Concept Videos
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
![Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F51444.jpg&w=3840&q=50)

