Simple and Practical Reductive Heck Protocol for Terminal Alkenes

Today our lab reports a new method for hydroarylation of aliphatic and heteroatom-substituted terminal alkenes with (hetero)aryl iodides via a reductive a Heck coupling approach.  A description of the work is available as a pre-print on ChemRxiv (click here).  This reaction is trivial to set up, as it can be performed on the benchtop and uses exclusively reagents that are commercially available and commonly available in a standard organic chemistry lab. The transformation is notable for its compatibility with a myriad of functional groups, including those that are potentially reductively sensitive (epoxides, ketones, aldehydes, etc.) as well various aza-heterocycles commonly required in drug discovery. Key to the successful of this reaction is use of a high PPh3:Pd (10:1) ratio to suppress undesired beta-hydride elimination. Kudos to John who took on this significant challenge single-handedly and overcame numerous obstacles to bring this idea to fruition!