Hydrogen-Transfer-Mediated α-Functionalization of 1,8-Naphthyridines by a Strategy Overcoming the Over-Hydrogenation Barrier

作者：Chen, Xiu-Wen; Zhao, He; Chen, Chun-Lian; Jiang, Huan-Feng; Zhang, Min^*

来源：Angewandte Chemie - International Edition, 2017, 56(45): 14232-14236.

DOI：10.1002/anie.201707702

• 1,8-naphthyridines
• hydrogen donor
• iridium catalysis
• tetrahydroquinolines
• transfer hydrogenative coupling

A general catalytic hydrogen transfer-mediated alpha-functionalization of 1,8-naphthyridines is reported for the first time that benefits from a hydrogen transfer-mediated activation mode for non-activated pyridyl cores. The pyridyl a-site selectively couples with the C8-site of various tetrahydroquinolines (THQs) to afford novel alpha-functionalized tetrahydro 1,8-naphthyridines, a class of synthetically useful building blocks and potential candidates for the discovery of therapeutic and bio-active products. The utilization of THQs as inactive hydrogen donors (HDs) appears to be a key strategy to overcome the over-hydrogenation barrier and address the chemoselectivity issue. The developed chemistry features operational simplicity, readily available catalyst and good functional group tolerance, and offers a significant basis for further development of new protocols to directly transform or functionalize inert N-heterocycles.

• 出版日期2017-11-6
• 单位华南理工大学