Intramolecular Addition of a Dimethylamino C(sp3)–H Bond across C–C Triple Bonds using IrCl(DTBM-SEGPHOS)(ethylene) Catalyst: Synthesis of Indoles from 2-Alkynyl-N-methylanilines

Synthesis ◽

10.1055/a-1511-1025 ◽

2021 ◽

Author(s):

Toshimichi Ohmura ◽

Kaito Yagi ◽

Takeru Torigoe ◽

Michinori Suginome

Keyword(s):

Double Bond ◽

Triple Bond ◽

Iridium Complex ◽

Dimethylamino Group ◽

Catalyst Synthesis ◽

Double Bond Isomerization ◽

Triple Bonds ◽

High Yields

Intramolecular addition of a C(sp3)–H bond of a dimethylamino group across a C–C triple bond in 2-alkynyl-N,N-dimethylanilines was effectively catalyzed by a new iridium complex IrCl(DTBM-SEGPHOS)(C2H4) in mesitylene at 150 °C. The intramolecular C(sp3)–H addition was followed by double bond isomerization to afford 3-substituted indoles in good to high yields.

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Some alkali metal alkyl amides as alkyne isomerization reagents: selective isomerization of one triple bond of a diynol

Canadian Journal of Chemistry ◽

10.1139/v83-189 ◽

1983 ◽

Vol 61 (6) ◽

pp. 1073-1076 ◽

Cited By ~ 15

Author(s):

Suzanne R. Abrams ◽

Donato D. Nucciarone ◽

Warren F. Steck

Keyword(s):

Sex Pheromone ◽

Alkali Metal ◽

Sodium Salt ◽

Triple Bond ◽

Lithium Salt ◽

Terminal Position ◽

Sodium Salts ◽

Triple Bonds ◽

High Yields ◽

Insect Sex

The lithium and sodium salts of 1,2-diaminoethane, 1,3-diaminopropane, n-butylamine, and the lithium salt of isobutylamine were studied as potential reagents for isomerization of triple bonds in alkyn-1-ols. The sodium salts of the diamines afforded high yields of the ω-alkyn-1-ol. Somewhat surprisingly, the sodium salt of n-butylamine also effects isomerization to the terminal position. The lithium salt of 1,3-diaminopropane gave the highest conversion of 2- to 3-alkyn-1-ol. A novel, selective rearrangement of one triple bond of a diynol, a 2, ω- to 3, ω-diyn-1-ol isomerization, was incorporated into a synthesis of the insect sex pheromone 3,13-octadecadienol acetate.

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12-Tungstophosphate Acids: An Efficient, Green and Recyclable Photocatalyst in Carbon-Carbon Double Bond Isomerization on Linear Alpha Olefins

Journal of Biomedical Research & Environmental Sciences ◽

10.37871/jbres1367 ◽

2021 ◽

Vol 2 (11) ◽

pp. 1170-1175

Author(s):

Wangjing Ma ◽

Xiao TC ◽

Liu BN ◽

Xu ZC ◽

Jin ZQ ◽

...

Keyword(s):

Double Bond ◽

High Selectivity ◽

Environmentally Friendly ◽

Recyclable Catalyst ◽

Double Bond Isomerization ◽

Carbon Double Bond ◽

Uv Visible ◽

Recyclable Photocatalyst ◽

High Yields ◽

Alpha Olefins

The accelerated UV visible photocatalytic carbon-carbon double bond isomerization of Linear Alpha Olefins (LAO) with 12-Tungstophosphate Acids (12-TPA) as an efficient, environmentally-friendly and recyclable catalyst was described, which produced the corresponding Linear Internal Olefins (LIO) in general high selectivity and high yields.

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Mechanisms of Double-Bond Isomerization Reactions of n-Butene on Different Lewis Acids

ACS Catalysis ◽

10.1021/acscatal.1c02846 ◽

2021 ◽

pp. 11293-11304

Author(s):

Fengjiao Yi ◽

Peng He ◽

Huimin Chen ◽

Yurong He ◽

Zhichao Tao ◽

...

Keyword(s):

Double Bond ◽

Lewis Acids ◽

Double Bond Isomerization

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Double bond isomerization of ethyl linoleate and vegetable oils to conjugated derivatives over an LDH supported ruthenium catalyst

RSC Advances ◽

10.1039/c5ra04822b ◽

2015 ◽

Vol 5 (45) ◽

pp. 36075-36082 ◽

Cited By ~ 2

Author(s):

Sivashunmugam Sankaranarayanan ◽

Gobi Selvam ◽

Kannan Srinivasan

Keyword(s):

Double Bond ◽

Vegetable Oils ◽

Ethyl Linoleate ◽

Ruthenium Catalyst ◽

Reaction Conditions ◽

Double Bond Isomerization

Isomerization of ethyl linoleate and vegetable oils to conjugated derivatives is achieved over an MgAl-LDH supported ruthenium catalyst under mild reaction conditions.

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