Unknown

Dataset Information

0

Copper-catalysed benzylic C-H coupling with alcohols via radical relay enabled by redox buffering.


ABSTRACT: Cross-coupling reactions enable rapid, convergent synthesis of diverse molecules and provide the foundation for modern chemical synthesis. The most widely used methods employ sp2-hybridized coupling partners, such as aryl halides or related pre-functionalized substrates. Here, we demonstrate copper-catalysed oxidative cross coupling of benzylic C-H bonds with alcohols to afford benzyl ethers, enabled by a redox-buffering strategy that maintains the activity of the copper catalyst throughout the reaction. The reactions employ the C-H substrate as the limiting reagent and exhibit broad scope with respect to both coupling partners. This approach to direct site-selective functionalization of C(sp3)-H bonds provides the basis for efficient three-dimensional diversification of organic molecules and should find widespread utility in organic synthesis, particularly for medicinal chemistry applications.

SUBMITTER: Hu H 

PROVIDER: S-EPMC7197765 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature

altmetric image

Publications

Copper-catalysed benzylic C-H coupling with alcohols via radical relay enabled by redox buffering.

Hu Huayou H   Chen Si-Jie SJ   Mandal Mukunda M   Pratik Saied Md SM   Buss Joshua A JA   Krska Shane W SW   Cramer Christopher J CJ   Stahl Shannon S SS  

Nature catalysis 20200224 4


Cross-coupling reactions enable rapid, convergent synthesis of diverse molecules and provide the foundation for modern chemical synthesis. The most widely used methods employ sp<sup>2</sup>-hybridized coupling partners, such as aryl halides or related pre-functionalized substrates. Here, we demonstrate copper-catalysed oxidative cross coupling of benzylic C-H bonds with alcohols to afford benzyl ethers, enabled by a redox-buffering strategy that maintains the activity of the copper catalyst thro  ...[more]

Similar Datasets

| S-EPMC6385223 | biostudies-literature
| S-EPMC5488708 | biostudies-literature
| S-EPMC5732067 | biostudies-literature
| S-EPMC5461486 | biostudies-literature
| S-EPMC4844805 | biostudies-literature
| S-EPMC8163310 | biostudies-literature
| S-EPMC5940001 | biostudies-literature
| S-EPMC8376995 | biostudies-literature
| S-EPMC8169770 | biostudies-literature
| S-EPMC3583361 | biostudies-literature