Highly selective single and multiple deuteration of unactivated C(sp3)-H bonds

Nian Li, Jinhang Li, Mingzhe Qin, Jiajun Li, Jie Han, Chengjian Zhu (), Weipeng Li () and Jin Xie ()
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Nian Li: Nanjing University
Jinhang Li: Nanjing University
Mingzhe Qin: Nanjing University
Jiajun Li: Nanjing University
Jie Han: Nanjing University
Chengjian Zhu: Nanjing University
Weipeng Li: Nanjing University
Jin Xie: Nanjing University

Nature Communications, 2022, vol. 13, issue 1, 1-8

Abstract: Abstract Selective deuteration of unactivated C(sp3)-H bonds is a highly attractive but challenging subject of research in pharmaceutical chemistry, material science and synthetic chemistry. Reported herein is a practical, highly selective and economical efficient hydrogen/deuterium (H/D) exchange of unactivated C(sp3)-H bonds by synergistic photocatalysis and hydrogen atom transfer (HAT) catalysis. With the easily prepared PMP-substituted amides as nitrogen-centered radical precursors, a wide range of structurally diverse amides can undergo predictable radical H/D exchange smoothly with inexpensive D2O as the sole deuterium source, giving rise to the distal tertiary, secondary and primary C(sp3)-H bonds selectively deuterated products in yields of up to 99% and excellent D-incorporations. In addition to precise monodeuteration, this strategy can also achieve multideuteration of the substrates contain more than one remote C(sp3)-H bond, which opens a method to address multi-functionalization of distal unactivated C(sp3)–H bonds.

Date: 2022
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DOI: 10.1038/s41467-022-31956-3

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