For our final blog assignment, we were asked to find a publication from Christina White's webpage and comment on the reaction and information we have learned throughtout the semester. After looking through the website I found a project where the Heck Reaction was explored. We learned about this recently in Chapter 26. During this reaction new C-C bonds are formed. C-C bond forming reactions are vital to the synthesis of natural products and pharmaceuticals. The intermolecular Heck reaction is unique among cross-coupling reactions due to the direct formation of C-C bonds from vinylic C-H bonds of alkenes. This report includes an intermolecular, oxidative Heck reaction catalyzed by a versatile Pd(II)/sulfoxide catalyst. A palldium catalyst is always used in these types of reactions. In general, a substitution reaction in which one H atom of the alkene starting material is replaced by the R' group of the vinyl or aryl halide. Several starting materials like homoallylic carbonyl compounds, bis-homoallylic carbonyl componds, alcohols, and thiols were used to synthesize a compound with a new C-C bond. Most of the details in this publication were hard for me to understand because they were things that we had not covered. The Heck Reaction was explored in greater detail than we had discussed in class. The material that I did understand consisted of alkenes, inductive effects, regioselectivity, substitution reactions, oxidation, and employing methods of synthesis. All of these things we have learned about throughout both semesters of Organic Chemistry. Follow the link below to check it out!
Sources:
- "A General and Highly Selective Chelate-Controlled Intermolecular Oxidative Heck Reaction." J.H. Delcamp; A.P. Brucks; and M.C. White JACS, 2008. http://www.scs.illinois.edu/white/pubs/pub11.pdf. (accessed May 5 2011).
- Smith, J.G; “Organic Chemistry;” Good-Hodge, T., Nemmers, D,. Eds.; McGraw-Hill: New York, 2008. Edition 2, pp 1009.
