金（I）催化的未活化末端和内部烯烃与 2-吡啶酮的分子内氢胺化反应。

Gold(I)-Catalyzed Intramolecular Hydroamination of Unactivated Terminal and Internal Alkenes with 2-Pyridones.

机构信息

French Family Science Center, Duke University , Durham, North Carolina 27708, United States.

出版信息

Org Lett. 2017 Mar 17;19(6):1466-1469. doi: 10.1021/acs.orglett.7b00450. Epub 2017 Mar 7.

DOI:10.1021/acs.orglett.7b00450

Abstract

The cationic gold phosphine complex [(P1)Au(NCMe)]SbF [P1 = P(t-Bu)o-biphenyl; 2] catalyzes the intramolecular hydroamination of 6-alkenyl-2-pyridones to form 1,6-carboannulated 2-pyridones in high yield. The hydroamination of 6-(γ-alkenyl)-2-pyridones was effective for monosubstituted and 1,1- and 1,2-disubstituted aliphatic alkenes, and the method was likewise effective for the hydroamination of 6-(δ-alkenyl)-2-pyridones. Spectroscopic analysis of mixtures of 6-(3-butenyl)-2-pyridone, (P1)AuCl, and AgSbF established the N-bound 2-hydroxypyridine complex [(P1)Au(NCH-2-OH-6-CHCHCH═CH)] SbF as the catalyst resting state.

摘要

阳离子金膦配合物[(P1)Au(NCMe)]SbF [P1 = P(t-Bu)o-biphenyl; 2] 可以催化 6-烯基-2-吡啶酮的分子内氨化反应，以高产率形成 1,6-碳环化的 2-吡啶酮。6-(γ-烯基)-2-吡啶酮的氨化反应对于单取代和 1,1-和 1,2-二取代脂肪族烯烃是有效的，该方法对于 6-(δ-烯基)-2-吡啶酮的氨化反应也是有效的。6-(3-丁烯基)-2-吡啶酮、(P1)AuCl 和 AgSbF 的混合物的光谱分析确立了 N-键合的 2-羟基吡啶配合物[(P1)Au(NCH-2-OH-6-CHCHCH═CH)] SbF 作为催化剂的静止状态。