CuBr-Catalyzed Direct Indolation of Tetrahydroisoquinolines via Cross-Dehydrogenative Coupling between sp3 C−H and sp2 C−H Bonds
Top Cited Papers
- 21 April 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 127 (19), 6968-6969
- https://doi.org/10.1021/ja0516054
Abstract
A novel and efficient C−C bond formation method was developed via the cross-dehydrogenative coupling (CDC) reaction of indoles and tetrahydroisoquinolines catalyzed by copper bromide in the presence of an oxidizing reagent, tert-BuOOH. The CDC reaction provides a simple and efficient catalytic method to construct indolyl tetrahydroisoquinolines via a combination of sp3 C−H bond and sp2 C−H bond followed by C−C bond formation.Keywords
This publication has 19 references indexed in Scilit:
- Highly Efficient Copper-Catalyzed Nitro-Mannich Type Reaction: Cross-Dehydrogenative-Coupling between sp3 C−H Bond and sp3 C−H BondJournal of the American Chemical Society, 2005
- Direct Coupling of Pyrroles with Carbonyl Compounds: Short Enantioselective Synthesis of (S)‐KetorolacAngewandte Chemie International Edition, 2005
- Simple indole alkaloids and those with a non-rearranged monoterpenoid unitNatural Product Reports, 2005
- Enantioselective, Copper(I)‐Catalyzed Three‐Component Reaction for the Preparation of PropargylaminesAngewandte Chemie International Edition, 2003
- News and ViewsPublished by Royal Society of Chemistry (RSC) ,2001
- The Atom Economy—A Search for Synthetic EfficiencyScience, 1991
- Practical synthesis of 5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-ol (cotarnine)The Journal of Organic Chemistry, 1990
- Ruthenium-catalyzed cytochrome P-450 type oxidation of tertiary amines with alkyl hydroperoxidesJournal of the American Chemical Society, 1988
- Synthesis of some 1-imidoyl-2-(3-indolyl)-1,2-dihydroquinolines and -isoquinolines via Reissert-type condensationsThe Journal of Organic Chemistry, 1975
- Reactions of Nitroparaffins with Pseudo Bases Related to Dihydroisoquinolinium HydroxideJournal of the American Chemical Society, 1949