Hu, X (Hu, Xia)^{[ 1 ]} ; Zhang, GT (Zhang, Guoting)^{[ 1 ]} ; Bu, FX (Bu, Faxiang)^{[ 1 ]} ; Lei, AW (Lei, Aiwen)^{[ 1,2 ]}

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 olefinsare 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.

作者关键词:photochemistry; hydration; anti-Markovnikov; alkene; alcohol; radical

KeyWords Plus:RH/RU DUAL CATALYST; PHOTOREDOX CATALYSIS; ORGANIC-SYNTHESIS; TANDEM HYDROFORMYLATION/HYDROGENATION; HYDROFUNCTIONALIZATION REACTIONS; SYNTHETIC APPLICATIONS; TERMINAL OLEFINS; PRIMARY ALCOHOLS; ALKENES; NUCLEOPHILE

通讯作者地址: Lei, AW (通讯作者)

Wuhan Univ, Inst Adv Studies, Coll Chem & Mol Sci, Wuhan 430072, Hubei, Peoples R China.

Chinese Acad Sci, Lanzhou Inst Chem Phys, Lanzhou 730000, Peoples R China.

地址:

电子邮件地址:aiwenlei@whu.edu.cn

原文PDF链接：

https://pubs.acs.org/doi/10.1021/acscatal.6b03388