68051-20-7Relevant academic research and scientific papers
Iron-catalyzed chemoselective cross-coupling of primary and secondary alkyl halides with arylzinc reagents
Nakamura, Masaharu,Ito, Shingo,Matsuo, Keiko,Nakamura, Eiichi
, p. 1794 - 1798 (2005)
Functional-group-compatible cross-coupling reaction of alkyl halides with arylzinc reagents takes place under iron catalysis in the presence of TMEDA, producing a variety of aromatic compounds in good to excellent yield. The pronounced effect of a magnesium salt was found to be the key to the promotion of the iron-catalyzed coupling reaction. Georg Thieme Verlag Stuttgart.
Inverting Conventional Chemoselectivity in the Sonogashira Coupling Reaction of Polyhalogenated Aryl Triflates with TMS-Arylalkynes
Wang, Miao,So, Chau Ming
, p. 681 - 685 (2022/01/20)
A newly developed phosphine ligand with a C2-cyclohexyl group on the indole ring was successfully applied in a chemoselective Sonogashira coupling reaction with excellent chemoselectivity, affording an inversion of the conventional chemoselectivity order of C–Br > C–Cl > C–OTf. This study also provided an efficient approach to the synthesis of polycyclic aromatic hydrocarbons (PAHs) and the natural product analogue trimethyl-selaginellin L by merging of chemoselective Sonogashira and Suzuki–Miyaura coupling reactions.
Phosphine ligand 2 - alkyl - indole skeleton as well as preparation method and application thereof
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, (2021/09/21)
The invention discloses a phosphine ligand 2 - alkyl - indole skeleton and a preparation method and application thereof, wherein the structural formula of the phosphine ligand 2 - alkyl - indole skeleton is shown I. , Wherein R. 1 . R2/su
Radical-based regioselective cross-coupling of indoles and cycloalkanes
Xiu, Jianmin,Yi, Wenbin
, p. 998 - 1002 (2016/02/27)
An investigation into the regiochemistry of radical functionalization of indoles using cycloalkanes through di-tert-butyl peroxide (DTBP)-promoted C(sp3)-H activation was conducted. A wide range of indoles bearing substituents at different positions was functionalized directly with simple cycloalkanes in moderate to high regioselectivity. 2-, 4- and 7-positions were mainly functionalized.
Anti-Markovnikov Hydroheteroarylation of Unactivated Alkenes with Indoles, Pyrroles, Benzofurans, and Furans Catalyzed by a Nickel-N-Heterocyclic Carbene System
Schramm, York,Takeuchi, Makoto,Semba, Kazuhiko,Nakao, Yoshiaki,Hartwig, John F.
supporting information, p. 12215 - 12218 (2015/10/12)
We report the catalytic addition of C-H bonds at the C2 position of heteroarenes, including pyrroles, indoles, benzofurans, and furans, to unactivated terminal and internal alkenes. The reaction is catalyzed by a combination of Ni(COD)2 and a sterically hindered, electron-rich N-heterocyclic carbene ligand or its analogous Ni(NHC)(arene) complex. The reaction is highly selective for anti-Markovnikov addition to α-olefins, as well as for the formation of linear alkylheteroarenes from internal alkenes. The reaction occurs with substrates containing ketones, esters, amides, boronate esters, silyl ethers, sulfonamides, acetals, and free amines.
Synthesis of indoles via alkylidenation of acyl hydrazides
Hisler, Kevin,Commeureuc, Aurélien G.J.,Zhou, Sheng-ze,Murphy, John A.
supporting information; experimental part, p. 3290 - 3293 (2009/08/17)
Indoles have been synthesised via alkylidenation of acyl phenylhydrazides using phosphoranes and the Petasis reagent, followed by in situ thermal rearrangement of the product enehydrazines. The Petasis reagent provides an essentially neutral equivalent of the [acid-catalysed] Fischer indole synthesis, but with acyl phenylhydrazides as starting substrates. Alkylidene triphenylphosphoranes convert aroyl phenylhydrazides to indoles, but acyl phenylhydrazides derived from aliphatic carboxylic acids undergo a Brunner reaction to form indolin-2-ones.
Intramolecular C-N bond addition of amides to alkynes using platinum catalyst
Shimada, Tomohiro,Nakamura, Itaru,Yamamoto, Yoshinori
, p. 10546 - 10547 (2007/10/03)
The intramolecular aminoacylation of alkynes using ortho-alkynylacetanilides proceeds in very high yields in the presence of PtCl2 catalyst. This reaction provides not only a useful procedure for synthesizing 2,3-disubstituted indoles at once from ortho-alkynylaniline derivatives, but also an interesting mechanistic aspect; the intramolecular C-N bond addition of amides to alkynes takes place readily in the presence of Pt(II) catalyst. Copyright
Investigation of the reaction of N-substituted indolylborates: Palladium catalyzed cross-coupling reactions and intramolecular alkyl migration reactions
Ishikura, Minoru,Agata, Isao,Katagiri, Nobuya
, p. 873 - 879 (2007/10/03)
The palladium catalyzed cross-coupling reaction of indolylborates with various N-protecting groups was investigated, where N-Methyl, N-methoxy, and N-tert-butoxycarbonyl groups were found to be useful. However, triethyl(1-methoxymethylindol-2- yl)borate could not be used for this reaction. It was also found that the alkyl migration reaction of trialkyl(1- methoxymethylindol-2-yl)borate produced 2-alkyl-1-methyl-indole accompanied by the unexpected reduction of 1-methoxymethyl group to 1-methyl group.
