Issue Date: May 12, 2008
Expanded Suzuki Cross-Coupling
The Suzuki reaction has proven to be an indispensible tool for organic chemists, allowing them to build complex molecules via the palladium- or nickel-catalyzed cross-coupling of organoboron compounds with a variety of electrophiles. Now, Gregory C. Fu and Bunnai Saito of MIT have expanded the scope of the Suzuki reaction by marrying unactivated alkyl electrophiles to organoboron reagents in an enantioselective manner (J. Am. Chem. Soc., DOI: 10.1021/ja8013677). Previous examples of enantioselective cross-coupling reactions of alkyl electrophiles required activated substrates, such as allylic or benzylic halides. Using a nickel diamine catalyst, Fu and Saito combined a variety of homobenzylic bromides with organoboron compounds to generate cross-coupled products enantioselectively (one example shown). The reaction uses commercially available catalyst components and proceeds under mild conditions, making it quite practical, the researchers note. "Although the process has limitations, its discovery demonstrates that unactivated alkyl electrophiles, a very important family of coupling partners, can begin to be considered as potential substrates for enantioselective cross-couplings," they write.
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