The February 9th, 2009 issue of Chemical and Engineering News featured a talk with Professor Jean-Claude Bradley, Drexel Univeristy, about some of his teams research projects and Open Notebook Science, in particular. Read the full article

Congratuations Jean-Claude !!

Sidenote: I had the pleasure of first meeting Professor Bradley via Second Life in early 2008. We happened to bump into each other one day at the American Chemical Society Island and then met in real life at the Spring 2008 ACS meeting. (Jean-Claude's avatar name is Horace Moody) Aldrich Chemistry has since become a sponsor for his Open Notebook Science challenge.  Additionally, together with Professor Andy Lang (Hiro Sheridan, avatar name) at Oral Roberts University they have created an interactive game for NMR in Second Life. Read more about that at the UsefulChemistry Blog.

A colleague just shared this posting from the New York Times Science section. It's a must see clip from a recent show with Conan O'Brien going off on the NYTimes about a correction that read:

Correction: February 4, 2009
An article on Tuesday about a newly discovered form of boron misstated the number of pure forms of the element. It is four, including the new one, not three.

http://tinyurl.com/b8reox

Enjoy!!

The hydration of alkynes has been extensively studied for more than 100 years. This reation allows the access to various carbonyl derivatives starting from alkynes. Nolan and coworkers reported the acid-free catalyzed alkyne hydration using a gold catalyst. Nolan has been one of the pioneer in the use of N-heterocyclic carbene (NHC) as ligands in various catalytic transformation using a variety of metals. Using a gold-NHC complex and silver hexafluoroantimonate, the authors demonstrated the outstanding activity of this catalyst in the hydration of various alkynes using 1,4-dioxane and methanol as reaction media. It is important to note that acid is not needed for this transformation and that catalyst loadings as low as 10 ppm were used for this reaction. 

Written by: Dr. Sharbil J. Firsan

Castillón, Claver, and co-authors have reported a new synthesis of air-stable and water-soluble zwitterionic phosphine ligands and their application in the Suzuki–Miyaura cross-coupling reaction in neat, non-dearated water.   For aryl bromides and arylboronic acids, this palladium-catalyzed reaction took place with high conversions, with and without microwave irradiation, and was characterized by very low catalyst loadings (0.025–0.05 mol %) and relatively short reaction times.  In the case of the much less reactive aryl chlorides, the reaction with arylboronic acids proceeded under microwave irradiation and low catalyst loadings (0.2–2.0 mol %), but resulted in only moderate conversions.

(1) García Suárez, E. J.; Ruiz, A.; Castillón, S.; Oberhauser, W.; Bianchini, C.; Claver, C. Dalton Trans. 2007, 2859.  (2) For a recent review on transition-metal-catalyzed cross-couplings in water, see Lipshutz, B. H.; Ghorai, S. Aldrichimica Acta 2008, 41, 59.

Aurrecoechea and coworkers have demonstrated a one pot oxypalladation/Heck reaction for the preparation of 3-alkenylbenzofurans in the presence of PdCl₂, KI, and DMF. This modular and efficient protocol utilizes air as the oxidant of the Pd⁰ generated after the Heck reaction. The preparation of these often biologically active moieties is usually accomplished via Wittig reaction of the necessary 3-formyl precursors or Heck reactions of the 3-halobenzofurans. The substrate scope was examined and the reaction was found to be quite general with respect to both the alkynyl phenol (both alkyl and aryl electron-poor and -rich substituents are acceptable) as well as the olefin coupling partner (alpha,beta-unsaturated esters, ketones, amides, nitriles, and sulfones, and styrenes were all tolerated).

Martinez, C.; Alvarez, R.; Aurrecoechea, J. M. Org. Lett. ASAP.

Written By: Mark Redlich, Ph.D.

Here is a recent report I came across which highlighted the NHC-catalyzed ring expansion of heterocyclic carboxaldehydes to provide lactones.  The best results were achieved when the 2,6-diisopropylphenyl substituted imidazolinium catalyst was employed.  Thiazolium and triazolium catalysts were also screened in the transformation but both provided either complex reaction mixtures or trace amounts of lactone.  Five-, six-, and seven-membered as well as bicyclic lactones are all accessible from their corresponding aldehydes, and the reaction is able to be performed under air without a significant decrease in yield.  Interestingly, the corresponding imidazolium NHC catalyst is ineffective in this transformation.

Wang, L. et al. Org. Lett. 2009, 11, ASAP.