Interest in the reductive cross-coupling of electrophilic reagents has increased dramatically over the past decade. In particular, the ability to selectively cross-couple aryl halides with alkyl halides avoids the need to prepare expensive and reactive organometallic reagents. The economic and environmental benefits of cross-electrophile coupling are further demonstrated by its non-reliance on precious metals catalysts, instead allowing the use inexpensive nickel catalysts.The coupling of nitrogen-containing heterocycles, which are pervasive in medicinal chemistry, represent a significant challenge. While 2-halopyridines have been coupled in good yield, the disparate electronic properties of variously substituted N-heterocycles has made finding a single catalyst system capable of coupling a broad range of halogenated heterocycles with alkyl halides a significant challenge. Herein, we report our recent progress in this area, including insight into why these substrates present such a challenge and how these obstacles might be overcome.

Reductive coupling of N-heterocycles: Challenges and mechanistic insights

248th National Meeting (2014)

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