Because the terminology and some aspects of this process can get pretty confusing, this post is going to explain alkene (olefin) metathesis in informal language. At least in the first part, so we can get a simplified introduction. Alkene metathesis … Read more
Transmetallation is the transfer of an organic group (ligand) from one metal to another during catalyzed cross-coupling reactions. It is one step in the catalytic cycle of palladium-catalyzed cross-coupling reactions, occurring between oxidative addition and reductive elimination. For example, this … Read more
Negishi coupling is one of the earliest and most important palladium-catalyzed cross-coupling reactions, enabling the formation of C–C bonds between organic halides and organozinc reagents. So, the two carbon fragments that are being coupled are an organozinc reagent (organozinc compound) … Read more
The Stille reaction is a Pd-catalyzed cross-coupling reaction between an organostannane (organotin compound) and an organic electrophile, typically an aryl or vinyl halide (or triflate). The organostannane may contain aryl, vinyl, alkynyl, allyl, or benzyl groups, and the reaction forms … Read more
The Suzuki reaction is a palladium-catalyzed cross-coupling reaction between an organoboron compound, such as a boronic acid or boronic ester, and an organic halide or triflate, forming a new C(sp2)-C(sp2) bond: Â Â This should not look much different from … Read more
The Sonogashira reaction couples a terminal alkyne with an aryl or vinyl halide (or triflate), forming a new C(sp)-C(sp2) bond. The reaction is catalyzed by palladium, typically in the presence of a copper(I) co-catalyst and an amine base, and is … Read more
In the previous post, we discussed the general features of transition metal-catalyzed cross-coupling reactions by listing the Heck, Suzuki, Stille, and Sonogashira reactions. The big picture we learned about these cross-coupling reactions is that the transition metal, namely Pd, serves … Read more
Cross-coupling reactions are carbon-carbon bond-forming reactions that join two organic molecules together. These reactions are catalyzed by transition metals such as palladium, nickel, copper, and iron, which is why they are also called transition metal-catalyzed cross-coupling reactions. Here are some … Read more
