Anti-Markovnikov hydroamination of alkenes with aqueous ammonia by metal-loaded titanium oxide photocatalyst,Journal of the American Chemical Society

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Anti-Markovnikov hydroamination of alkenes with aqueous ammonia by metal-loaded titanium oxide photocatalyst
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2020-06-22 , DOI: 10.1021/jacs.0c04598
Soyeong Park ₁ , Jaeyoung Jeong ₁ , Ken-Ichi Fujita ₁ , Akira Yamamoto _{1,

2} , Hisao Yoshida _{1,

2}

Affiliation

A completely new route was established to synthesize valuable primary amines from alkenes by using aqueous ammonia, that is, a simple photocatalytic hydroamination of alkenes using aqueous ammonia with a metal-loaded TiO2 photocata-lyst. Although the photochemical hydroamination prefers to form amines according to Markovnikov rule, the new photo-catalytic hydroamination gives anti-Markovnikov products predominantly. With an Au-loaded TiO2 photocatalyst, the amine yield reached up to 93% and the regioselectivity of anti-Markovnikov products was above 98%. The reaction mechanism was proposed for the new photocatalytic hydroamination.

中文翻译：

负载金属的氧化钛光催化剂对烯烃与氨水的反马尔科夫尼科夫加氢胺化反应

建立了一条全新的路线，通过使用氨水从烯烃合成有价值的伯胺，即使用氨水和负载金属的 TiO2 光催化剂对烯烃进行简单的光催化加氢胺化。尽管根据马尔可夫尼科夫规则光化学加氢胺化更倾向于形成胺，但新的光催化加氢胺化主要产生抗马尔可夫尼科夫产物。使用负载金的 TiO2 光催化剂，胺产率高达 93%，抗马尔科夫尼科夫产物的区域选择性在 98% 以上。提出了新型光催化加氢胺化的反应机理。

更新日期：2020-06-22

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