Transition-metal-catalyzed cross coupling is commonly used in organic synthesis for the production of fine chemicals. In particular, sp2–sp3 cross coupling has been a vibrant area of research, typically used for complex fragment coupling.
Stephen L. Buchwald, Massachusetts Institute of Technology (MIT), Cambridge, USA, and colleagues have developed a complementary method for sp2–sp3 cross coupling by using a combination of copper(I) hydride (CuH) and palladium catalysis. This method allows terminal olefins, a common and widely available class of chemicals, to couple with aryl halides by an anti-Markovnikov hydroarylation with high efficiency and regioselectivity (example product pictured).
The protocol has been shown to work for a broad range of substrates containing a variety of functional groups. Screening of cyclic alkenes also demonstrates that cyclopentene is an effective coupling partner under similar reaction conditions. Importantly, this method removes the need for stoichiometric metal reagents, which can often be air- and water-sensitive and require multistep synthetic routes.
Article Views: 2586
Please note that to comment on an article you must be registered and logged in.
Registration is for free, you may already be registered to receive, e.g., the newsletter. When you register on this website, please ensure you view our terms and conditions. All comments are subject to moderation.