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C2-Alkylation and Alkenylation of Indoles Catalyzed by a Low-Valent Cobalt Complex in the Absence of Reductant
- Source :
- Organic Letters, Organic Letters, 2016, 18 (9), pp.2292-2295. ⟨10.1021/acs.orglett.6b00939⟩, Organic Letters, American Chemical Society, 2016, 18 (9), pp.2292-2295. ⟨10.1021/acs.orglett.6b00939⟩
- Publication Year :
- 2016
- Publisher :
- HAL CCSD, 2016.
-
Abstract
- International audience; Herein an extremely versatile, well-defined, low-valent cobalt catalyst [Co(PMe3)(4)] capable of intermolecular and intramolecular imine-directed C2-alkylation and alkenylation of indoles is reported. The reaction proceeds in the absence of reducing agents or additives, affording a range of substituted indoles and dihydropyrroloindoles in high yields and regioselectivities. With the aid of deuterium labeling studies and DFT (Density Functional Theory) calculations, a mechanism is proposed that is based on a Ligand-to-Ligand Hydrogen Transfer pathway.
- Subjects :
- inorganic chemicals
010405 organic chemistry
Reducing agent
[CHIM.ORGA]Chemical Sciences/Organic chemistry
Organic Chemistry
Intermolecular force
chemistry.chemical_element
Alkylation
010402 general chemistry
01 natural sciences
Biochemistry
Combinatorial chemistry
0104 chemical sciences
Catalysis
Deuterium
chemistry
Intramolecular force
Organic chemistry
Density functional theory
Physical and Theoretical Chemistry
Cobalt
Subjects
Details
- Language :
- English
- ISSN :
- 15237060 and 15237052
- Database :
- OpenAIRE
- Journal :
- Organic Letters, Organic Letters, 2016, 18 (9), pp.2292-2295. ⟨10.1021/acs.orglett.6b00939⟩, Organic Letters, American Chemical Society, 2016, 18 (9), pp.2292-2295. ⟨10.1021/acs.orglett.6b00939⟩
- Accession number :
- edsair.doi.dedup.....0dea33d5bbcc4cbde6bb46d9ae95354a