Highly Regioselective Copper-Catalyzed Transfer Hydrodeuteration of Unactivated Terminal Alkenes

被引：14

作者：

Reyes, Albert ^{[1
]}

Torres, Emanuel Rivera ^{[1
]}

Vang, Zoua Pa ^{[1
]}

Clark, Joseph R. ^{[1
]}

机构：

[1] Marquette Univ, Dept Chem, Milwaukee, WI 53233 USA

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2022年 / 28卷 / 09期

关键词：

alkene hydrofunctionalization; copper catalysis; deuterated alkanes; transfer hydrodeuteration; TRANSFER HYDROGENATION; DEUTERIUM; DRUG; HD; STEREOCHEMISTRY; MECHANISM; OLEFINS;

D O I：

10.1002/chem.202104340

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Catalytic transfer hydrodeuteration of unactivated alkenes is challenging because of the requirement that chemically similar hydrogen and deuterium undergo selective insertion across a pi-bond. We now report a highly regioselective catalytic transfer hydrodeuteration of unactivated terminal alkenes across a variety of heteroatom- or heterocycle-containing substrates. The base-metal-catalyzed reaction is also demonstrated on two complex natural products. Reaction studies indicate modular conditions that can also be extended to perform either an alkene transfer hydrogenation or transfer deuteration.

引用

页数：5

共 52 条

[1] Stereochemistry of the singlet oxygenation of simple alkenes: A stereospecific transformation [J].