Title:

"New Electrophiles, Strategies, and Catalysts for Cross-Electrophile Coupling"

Abstract. The primary challenge for synthetic chemists is supporting the efficient exploration of chemical space to find the best molecules for understanding or solving problems. In the past decade, cross-electrophile coupling, the union of two different electrophiles through transition-metal catalysis under reducing conditions, has become an increasingly used tool in these efforts. By focusing method development on the largest pools of pre-functionalized molecules, the millions of available carbon electrophiles, chemical space can be more efficiently accessed than through reactions limited to the thousands of carbon nucleophiles. Development of these reactions requires the development of strategies to utilize the most abundant electrophile pools and to ensure the reactions favor the cross-coupled product over potential homodimeric products. Guided by mechanistic understanding, we have developed general strategies tailored to C(sp2)-C(sp2), C(sp2)-C(sp3), and C(sp3)-C(sp3) bond formation based upon differential modes of activation (two-electron vs single-electron), multimetallic catalysis, and utilizing the general idea of persistent vs transient intermediates. This talk will briefly introduce the mechanistic underpinnings of selectivity in cross-electrophile coupling reactions for C(sp2)-C(sp3) bond formation and then discuss recent developments in the design of better catalysts, new electrophiles, and new reactions. In particular, this talk will explore new uses of electrophiles derived from carboxylic acids and less reactive electrophiles, such as organic chlorides and sulfonate esters. Another focus will be the reductant approach (chemical, electrochemical, photochemical) and its implications for reactivity. Finally, applications to industrial challenges both large and small will be presented.

• This event is part of the Baker Lecture Series