Journal
GREEN CHEMISTRY
Volume 23, Issue 22, Pages 8988-8994Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1gc02805g
Keywords
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Funding
- National Natural Science Foundation of China [21502135]
- Natural Science Foundation of Shanxi [201901D111081]
- Scientific and Technological Innovation Programs of Higher Education Institutions in Shanxi [201802024]
- Fund Program for the Scientific Activities of Selected Returned Overseas Professionals in Shanxi Province
- Shanxi Scholarship Council of China [2020-029]
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A synergistic combination of photoredox and polarity reversal catalysis enabled a novel approach for the generation of silyl cation via visible-light photoredox catalysis, facilitating the dehydrogenative cross-coupling of Si-H and O-H in good yields and broad substrate scope. The reaction proceeded smoothly without the need for any metals, external oxidants, or proton reductants, unlike traditional photocatalytic hydrogen evolution cross-coupling reactions.
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 requirement 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.
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