Metal-free hydrogen evolution cross-coupling enabled by synergistic photoredox and polarity reversal catalysis
- 12 October 2021
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Green Chemistry
- Vol. 23 (22), 8988-8994
- https://doi.org/10.1039/d1gc02805g
Abstract
A synergistic combination of photoredox and polarity reversal catalysis enabled a hydrogen evolution cross-coupling of silanes with H2O, alcohols, phenols, and silanols, which afforded the corresponding silanols, monosilyl ethers, and disilyl ethers respectively in moderate to excellent yields. The dehydrogenative cross-coupling of Si−H and O−H proceeded smoothly with broad substrate scope and good functional group compatibility in the presence of only an organophotocatalyst 4-CzIPN and a thiol HAT catalyst, without the requirements of any metals, external oxidants and proton reductants, which is distinct from the previously reported photocatalytic hydrogen evolution cross-coupling reactions where a proton reduction cocatalyst such as a cobalt complex is generally required. Mechanistically, a silyl cation intermediate is generated to facilitate the cross-coupling reaction, which therefore represents an unprecedented approach for the generation of silyl cation via visible-light photoredox catalysis.Funding Information
- National Natural Science Foundation of China (21502135)
- Natural Science Foundation of Shanxi Province (201901D111081)
- Program for the Scientific Activities of Selected Returned Overseas Professionals in Shaanxi Province (2020-029)
- Shanxi Scholarship Council of China
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