Photobromination of Alkyl Halides, an Unusual Orienting Effect in the Bromination of Alkyl Bromides

1963 ◽  
Vol 85 (17) ◽  
pp. 2607-2613 ◽  
Author(s):  
Warren. Thaler
Keyword(s):  
Alkyl Halides ◽  
Alkyl Bromides ◽  
Orienting Effect

scholarly journals Dehalogenation of functionalized alkyl halides in water at room temperature

2015 ◽  
Vol 17 (2) ◽  
pp. 893-897 ◽  
Author(s):  
Nicholas A. Isley ◽  
Matt S. Hageman ◽  
Bruce H. Lipshutz
Keyword(s):  
Room Temperature ◽  
Alkyl Halides ◽  
Alkyl Bromides ◽  
Green Conditions

Alkyl bromides and chlorides can be reduced to the corresponding hydrocarbons utilizing zinc in the presence of an amine additive under very mild, green conditions.

ChemInform Abstract: Indium(III)-Catalyzed Reductive Bromination and Iodination of Carboxylic Acids to Alkyl Bromides and Iodides: Scope, Mechanism, and One-Pot Transformation to Alkyl Halides and Amine Derivatives.

ChemInform ◽  
2014 ◽  
Vol 45 (15) ◽  
pp. no-no
Author(s):  
Toshimitsu Moriya ◽  
Shinichiro Yoneda ◽  
Keita Kawana ◽  
Reiko Ikeda ◽  
Takeo Konakahara ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Alkyl Halides ◽  
One Pot ◽  
Alkyl Bromides

scholarly journals Photocatalytic α-Alkylation of Amines with Alkyl Halides

2020 ◽  
Author(s):  
Lingying Leng ◽  
Joseph Ready
Keyword(s):  
Organic Synthesis ◽  
Nucleophilic Addition ◽  
Building Blocks ◽  
Alkyl Halides ◽  
Organometallic Reagents ◽  
Dehydrogenative Coupling ◽  
Alkyl Bromides ◽  
Alternative Approach ◽  
Traditionally Prepared ◽  
Carbon Centered Radical

a-Branched amines represent essential building blocks for organic synthesis. They are traditionally prepared through nucleophilic addition to imines. These methods often require highly reactive organometallic reagents and proceed under rigorous air- and moisture-free conditions. Here we describe an alternative approach that involves a net dehydrogenative coupling between alkyl bromides and amines. Mechanistically, the reaction likely involves photocatalytic generation of an a-amino radical and a stabilized carbon-centered radical (allyl, benzyl, a-carbonyl) followed by radical recombination. This approach offers a mild, atom-economical, redox neutral synthesis of a-branched amines that shows broad scope and avoids pre-metalated reagents.

Indium(III)-Catalyzed Reductive Bromination and Iodination of Carboxylic Acids to Alkyl Bromides and Iodides: Scope, Mechanism, and One-Pot Transformation to Alkyl Halides and Amine Derivatives

2013 ◽  
Vol 78 (21) ◽  
pp. 10642-10650 ◽  
Author(s):  
Toshimitsu Moriya ◽  
Shinichiro Yoneda ◽  
Keita Kawana ◽  
Reiko Ikeda ◽  
Takeo Konakahara ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Alkyl Halides ◽  
One Pot ◽  
Alkyl Bromides

scholarly journals Direct C(sp2)–H alkylation of unactivated arenes enabled by photoinduced Pd catalysis

2020 ◽  
Vol 11 (1) ◽  
Author(s):  
Daeun Kim ◽  
Geun Seok Lee ◽  
Dongwook Kim ◽  
Soon Hyeok Hong
Keyword(s):  
Functional Group ◽  
Alkyl Halide ◽  
Alkyl Halides ◽  
Biologically Active ◽  
One Pot ◽  
Bond Forming ◽  
Alkyl Groups ◽  
Alkyl Bromides ◽  
Reaction Proceeds ◽  
Alkylation Reactions

AbstractDespite the fundamental importance of efficient and selective synthesis of widely useful alkylarenes, the direct catalytic C(sp2)–H alkylation of unactivated arenes with a readily available alkyl halide remains elusive. Here, we report the catalytic C(sp2)–H alkylation reactions of unactivated arenes with alkyl bromides via visible-light induced Pd catalysis. The reaction proceeds smoothly under mild conditions without any skeletal rearrangement of the alkyl groups. The direct syntheses of structurally diverse linear and branched alkylarenes, including the late-stage phenylation of biologically active molecules and an orthogonal one-pot sequential Pd-catalyzed C–C bond-forming reaction, are achieved with exclusive chemoselectivity and exceptional functional group tolerance. Comprehensive mechanistic investigations through a combination of experimental and computational methods reveal a distinguishable Pd(0)/Pd(I) redox catalytic cycle and the origin of the counter-intuitive reactivity differences among alkyl halides.

scholarly journals Nickel-catalyzed electrochemical carboxylation of unactivated aryl and alkyl halides with CO2

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Guo-Quan Sun ◽  
Wei Zhang ◽  
Li-Li Liao ◽  
Li Li ◽  
Zi-Hao Nie ◽  
...  
Keyword(s):  
Catalytic System ◽  
Functional Group ◽  
Alkyl Halides ◽  
Aryl Halides ◽  
Aryl Chlorides ◽  
Mild Conditions ◽  
Aryl Bromides ◽  
Alkyl Bromides ◽  
Pseudo Halides ◽  
Electrochemical Carboxylation

AbstractElectrochemical catalytic reductive cross couplings are powerful and sustainable methods to construct C−C bonds by using electron as the clean reductant. However, activated substrates are used in most cases. Herein, we report a general and practical electro-reductive Ni-catalytic system, realizing the electrocatalytic carboxylation of unactivated aryl chlorides and alkyl bromides with CO2. A variety of unactivated aryl bromides, iodides and sulfonates can also undergo such a reaction smoothly. Notably, we also realize the catalytic electrochemical carboxylation of aryl (pseudo)halides with CO2 avoiding the use of sacrificial electrodes. Moreover, this sustainable and economic strategy with electron as the clean reductant features mild conditions, inexpensive catalyst, safe and cheap electrodes, good functional group tolerance and broad substrate scope. Mechanistic investigations indicate that the reaction might proceed via oxidative addition of aryl halides to Ni(0) complex, the reduction of aryl-Ni(II) adduct to the Ni(I) species and following carboxylation with CO2.

Copper-catalysed direct radical alkenylation of alkyl bromides

2014 ◽  
Vol 12 (35) ◽  
pp. 6790-6793 ◽  
Author(s):  
Xu Zhang ◽  
Hong Yi ◽  
Zhixiong Liao ◽  
Guoting Zhang ◽  
Chao Fan ◽  
...  
Keyword(s):  
Alkyl Halides ◽  
Alkyl Bromides ◽  
Tertiary Alkyl

A copper-catalysed direct radical alkenylation of benzyl bromides and α-carbonyl alkyl bromides has been developed. Compared with recent radical alkenylations which mostly focused on secondary or tertiary alkyl halides, this transformation shows good reactivity towards primary alkyl halides and tertiary/secondary alkyl halides are also tolerated.

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