Small Molecule Process Chemistry, Genentech, Inc. , 1 DNA Way, South San Francisco, California 94080, United States.
Department of Chemistry, University of Wisconsin-Madison , 1101 University Avenue, Madison, Wisconsin 53706, United States.
Org Lett. 2016 Aug 5;18(15):3586-9. doi: 10.1021/acs.orglett.6b01592. Epub 2016 Jul 12.
A direct oxidative C-H amination affording 1-acetyl indolecarboxylates starting from 2-acetamido-3-arylacrylates has been achieved. Indole-2-carboxylates can be targeted with a straightforward deacetylation of the initial reaction products. The C-H amination reaction is carried out using a catalytic Pd(II) source with oxygen as the terminal oxidant. The scope and application of this chemistry is demonstrated with good to high yields for numerous electron-rich and electron-poor substrates. Further reaction of selected products via Suzuki arylation and deacetylation provides access to highly functionalized indole structures.
一种直接的氧化 C-H 胺化方法,从 2-乙酰氨基-3-芳基丙烯酰胺出发,得到 1-乙酰吲哚羧酸酯。吲哚-2-羧酸酯可以通过初始反应产物的直接脱乙酰化来靶向。C-H 胺化反应使用催化 Pd(II)源和氧气作为末端氧化剂进行。该化学方法的范围和应用通过许多富电子和缺电子底物的高产率得到了证明。通过 Suzuki 芳基化和脱乙酰化进一步反应选择的产物,可以获得高度官能化的吲哚结构。