Journal
ORGANIC LETTERS
Volume 22, Issue 3, Pages 1199-1203Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c00096
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Funding
- JSPS [JP18K14868]
- Teijin Pharma Award in Synthetic Organic Chemistry Japan
- Tokyo Biochemical Research Foundation
- Keihanshin Consortium for Fostering the Next Generation of Global Leaders in Research (K-CONNEX)
- Platform Project for Supporting Drug Discovery and Life Science Research [Basis for Supporting Innovative Drug Discovery and Life Science Research (BINDS)] from AMED [JP19am0101084]
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Herein, we describe the generation of an organochromium-type carbanion species from a non-activated C-H bond and its nucleophilic addition to aldehydes. The catalytic carbanion generation occurred through formal deprotonation of a non-activated C-H bond under mild conditions and did not need the prefunctionalization or anion stabilizing group. Carbon radical intermediates generated by decatungstate photocatalyst-mediated hydrogen abstraction were captured by a chromium salt with the reductive radical-polar crossover reaction to produce organochromium carbanions.
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