Bidentate, monoanionic auxiliary-directed functionalization of carbon-hydrogen bonds

Accounts of Chemical Research
Olafs DaugulisLy Dieu Tran

Abstract

In recent years, carbon-hydrogen bond functionalization has evolved from an organometallic curiosity to a tool used in mainstream applications in the synthesis of complex natural products and drugs. The use of C-H bonds as a transformable functional group is advantageous because these bonds are the most abundant functionality in organic molecules. One-step conversion of these bonds to the desired functionality shortens synthetic pathways, saving reagents, solvents, and labor. Less chemical waste is generated as well, showing that this chemistry is environmentally beneficial. This Account describes the development and use of bidentate, monoanionic auxiliaries for transition-metal-catalyzed C-H bond functionalization reactions. The chemistry was initially developed to overcome the limitations with palladium-catalyzed C-H bond functionalization assisted by monodentate directing groups. By the use of electron-rich bidentate directing groups, functionalization of unactivated sp(3) C-H bonds under palladium catalysis has been developed. Furthermore, a number of abundant base-metal complexes catalyze functionalization of sp(2) C-H bonds. At this point, aminoquinoline, picolinic acid, and related compounds are among the most used and v...Continue Reading

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Citations

Jan 9, 2016·Journal of the American Chemical Society·José A Fernández-SalasDavid J Procter
Feb 11, 2016·Organic Letters·Vinod G LandgeEkambaram Balaraman
Feb 20, 2016·Organic Letters·Gangam Srikanth Kumar, Manmohan Kapur
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Oct 5, 2016·Journal of the American Chemical Society·Chen KongTom G Driver
Oct 5, 2016·Organic Letters·Vinod G LandgeEkambaram Balaraman
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Oct 7, 2016·Journal of the American Chemical Society·Kin S YangKeary M Engle
Oct 26, 2016·Journal of the American Chemical Society·Zhen LiuKeary M Engle

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