Aerobic Pd-Catalyzed sp3 C-H Olefination: A Route to Both N-Heterocyclic Scaffolds and Alkenes

被引：192

作者：

Stowers, Kara J. ^{[1
]}

Fortner, Kevin C. ^{[1
]}

Sanford, Melanie S. ^{[1
]}

机构：

[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 17期

关键词：

CARBON-HYDROGEN BONDS; OXIDATIVE FUNCTIONALIZATION; COUPLING REACTION; CYCLIZATION; DERIVATIVES; ARYLATION;

D O I：

10.1021/ja2015586

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

This communication describes a new method for the Pd/polrxometalate-catalyzed aerobic olefination of unactivated sp(3)C H bonds. Nitrogen heterocycles serve as directing groups, and air is used as the terminal oxidant. The products undergo reversible intramolecular Michael addition, which protects the monoalkenylated product from overfunctionalization. Hydrogenation of the Michael adducts provides access to bicyclic nitrogen-containing scaffolds that are prevalent in alkaloid natural products. Additionally, the cationic Michael adducts undergo facile elimination to release alpha,beta-unsaturated olefins, which can be further elaborated via C-C and C-heteroatom bond-forming reactions.

引用

页码：6541 / 6544

页数：4

共 34 条

[31] Ligand-Enabled Reactivity and Selectivity in a Synthetically Versatile Aryl C-H Olefination [J].