Journal
ACS CATALYSIS
Volume 7, Issue 2, Pages 1432-1437Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.6b03388
Keywords
photochemistry; hydration; anti-Markovnikov; alkene; alcohol; radical
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Funding
- National Natural Science Foundation of China [21390400, 21520102003, 21272180, 21302148]
- Hubei Province Natural Science Foundation of China [2013CFA081]
- Research Fund for the Doctoral Program of Higher Education of China [20120141130002]
- Ministry of Science and Technology of China [2012YQ120060]
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Considering that stoichiometric borane and oxidant are required in the classical alkene anti-Markovnikov hydration process, it remains appealing to achieve the transformation in a catalytic protocol. Herein, a visible-light mediated anti-Markovnikov addition of water to alkenes by using an organic photoredox catalyst in conjunction with a redox-active hydrogen atom donor was developed, which avoided the need for a transition-metal catalyst, stoichiometric borane, as well as oxidant. Both terminal and internal olefins are readily accommodated in this transformation to obtain corresponding primary and secondary alcohols in good yields with single regioselectivity. This procedure can be scaled up to gram scale with a 230 turnover number based on photocatalyst.
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