Nickel-Catalyzed Multicomponent Coupling Reaction of Alkyl Halides, Isocyanides and H2O: An Expedient Way to Access Alkyl Amides

Synthesis ◽  
2020 ◽  
Vol 52 (22) ◽  
pp. 3466-3472
Author(s):  
Yunkui Liu ◽  
Bingwei Zhou ◽  
Qiao Li ◽  
Hongwei Jin
Keyword(s):  
Functional Group ◽  
Coupling Reaction ◽  
Alkyl Halides ◽  
Previous Literature ◽  
Catalytic Cycle ◽  
Reaction Conditions ◽  
Multicomponent Coupling ◽  
Easy Operation

We herein describe a Ni-catalyzed multicomponent coupling reaction of alkyl halides, isocyanides, and H2O to access alkyl amides. Bench-stable NiCl2(dppp) is competent to initiate this transformation under mild reaction conditions, thus allowing easy operation and adding practical value. Substrate scope studies revealed a broad functional group tolerance and generality of primary and secondary alkyl halides in this protocol. A plausible catalytic cycle via a SET process is proposed based on preliminary experiments and previous literature.

Copper(I)-Catalyzed Sulfenylation of 1,3-Dicarbonyl Substrates with Disulfides under Mild Conditions

Synlett ◽  
2019 ◽  
Vol 30 (19) ◽  
pp. 2181-2184 ◽  
Author(s):  
Jingnan Zhao ◽  
Fan Yang ◽  
Zongyi Yu ◽  
Xiaofei Tang ◽  
Yufeng Wu ◽  
...  
Keyword(s):  
Functional Group ◽  
Atom Economy ◽  
Reaction Conditions ◽  
Keto Esters ◽  
Mild Conditions ◽  
Easy Operation

A copper(I) iodine catalyzed sulfenylation of 1,3-dicarbonyl substrates in the presence of MeCN is presented. Various β-keto esters and β-keto amide substrates can react with disulfides to afford their corresponding products in good to excellent yields. The notable features of this protocol include high atom economy, easy operation, mild reaction conditions, and excellent functional group tolerance.

Dimerization of Aromatic Compounds Using Palladium-Carbon-Catalyzed Suzuki–Miyaura Cross-Coupling by One-Pot Synthesis

Synlett ◽  
2018 ◽  
Vol 29 (06) ◽  
pp. 779-784 ◽  
Author(s):  
Guoliang Chen ◽  
Fangyu Du ◽  
Qifan Zhou ◽  
Dongdong Liu ◽  
Ting Fang ◽  
...  
Keyword(s):  
Aromatic Compounds ◽  
Functional Group ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Potassium Acetate ◽  
Carbon Catalyst ◽  
Reaction Conditions ◽  
One Pot ◽  
Cross Coupling Reaction ◽  
High Yields

The aromatic dimers play a significant role in many aspects. Herein, we report a simple palladium-carbon catalyst that is highly effective for the dimerization of brominated aromatic compounds under mild conditions using abundant brominated aromatic compounds, bis(pinacolate)diboron and potassium acetate by a ‘one-pot’ method. This process, which we believe proceeds via a Suzuki–Miyaura cross-coupling reaction mechanism, allows access to a variety of aromatic compounds under mild reaction conditions and has a good functional group tolerance with moderate to high yields.

Functional Polysilanes and their Optical, Chiroptical and Photoluminescence Properties

2019 ◽  
Vol 6 (3) ◽  
pp. 193-221 ◽  
Author(s):  
Km. Meenu ◽  
Dibyendu S. Bag ◽  
Rekha Lagarkha ◽  
Radha Tomar ◽  
Arvind K. Gupta
Keyword(s):  
Functional Group ◽  
Photophysical Properties ◽  
Coupling Reaction ◽  
Functional Materials ◽  
Side Chain ◽  
Inorganic Polymers ◽  
Reaction Conditions ◽  
Wurtz Coupling ◽  
Single Material ◽  
Boiling Toluene

‘Polysilanes’ is an important class of inorganic polymers having Si-Si σ-conjugation along the backbone. They exhibit extraordinary electronic and photophysical properties and find suitable optoelectronics applications. They are typically synthesized by Wurtz coupling reaction of dichlorodialkylsilane or dichlorodiphenylsilane or dichloroalkylphenylsilane and their combinations under drastic reaction conditions by using sodium dispersion in boiling toluene. In such a drastic condition, no functional groups sustain with polysilane polymer. In order to achieve such functional materials, researchers have been interested in synthesizing functional polysilane with a different functional group like a chiral group, azobenzene containing chromophore and other heteroatoms in their main chain or side chain. Therefore, it is a very challenging task to synthesize polysilanes having effective functionality integrated with their structures. However, the modern technological demand of materials leads to efforts to obtain polymers having functional and multifunctional activity in a single material. In this review article, we cover the synthesis of polysilane with functional activity via pre-polymerization and post-polymerization with a functional group.

Ligand-free Cu-catalyzed odorless synthesis of unsymmetrical sulfides through cross-coupling reaction of aryl/benzyl/alkyl halides with an aryl boronic acid/S8 system as a thiolating agent in PEG

RSC Advances ◽  
2015 ◽  
Vol 5 (46) ◽  
pp. 37060-37065 ◽  
Author(s):  
Abed Rostami ◽  
Amin Rostami ◽  
Arash Ghaderi ◽  
Mohammad Ali Zolfigol
Keyword(s):  
Boronic Acid ◽  
Coupling Reaction ◽  
Alkyl Halides ◽  
Green Solvent ◽  
Reaction Conditions ◽  
One Pot ◽  
Cross Coupling Reaction ◽  
Ligand Free ◽  
One Step ◽  
Aryl Boronic Acid

Efficient one-pot, one-step synthesis of unsymmetrical sulfides has been reported under mild reaction conditions with good yields in green solvent.

scholarly journals Tandem Photoredox Catalysis: Enabling Carbonylative Amidation of Aryl and Alkylhalides

2020 ◽  
Author(s):  
José Augusto Forni ◽  
NENAD MICIC ◽  
Timothy Connell ◽  
GEETHIKA WERAGODA ◽  
Anastasios Polyzos
Keyword(s):  
Natural Products ◽  
Late Stage ◽  
Aromatic Amines ◽  
Functional Group ◽  
Alkyl Halides ◽  
Catalytic Cycle ◽  
Aryl Bromides ◽  
Alkyl Iodides ◽  
Tertiary Alkyl

<p>We report a new visible light-mediated carbonylative amidation of aryl, heteroaryl and alkyl halides. A tandem catalytic cycle of [Ir(ppy)<sub>2</sub>(dtb-bpy)]<sup>+</sup> generates a potent iridium photoreductant via a second catalytic cycle in the presence of DIPEA which productively engages aryl bromides, iodides and even chlorides as well as primary, secondary and tertiary alkyl iodides. The versatility of the in-situ generated catalyst is illustrated by compatibility with aliphatic and aromatic amines, high functional group tolerance and the late-stage amidation of complex natural products. </p>

scholarly journals Tandem Photoredox Catalysis: Enabling Carbonylative Amidation of Aryl and Alkylhalides

2020 ◽  
Author(s):  
José Augusto Forni ◽  
NENAD MICIC ◽  
Timothy Connell ◽  
GEETHIKA WERAGODA ◽  
Anastasios Polyzos
Keyword(s):  
Natural Products ◽  
Late Stage ◽  
Aromatic Amines ◽  
Functional Group ◽  
Alkyl Halides ◽  
Catalytic Cycle ◽  
Aryl Bromides ◽  
Alkyl Iodides ◽  
Tertiary Alkyl

<p>We report a new visible light-mediated carbonylative amidation of aryl, heteroaryl and alkyl halides. A tandem catalytic cycle of [Ir(ppy)<sub>2</sub>(dtb-bpy)]<sup>+</sup> generates a potent iridium photoreductant via a second catalytic cycle in the presence of DIPEA which productively engages aryl bromides, iodides and even chlorides as well as primary, secondary and tertiary alkyl iodides. The versatility of the in-situ generated catalyst is illustrated by compatibility with aliphatic and aromatic amines, high functional group tolerance and the late-stage amidation of complex natural products. </p>

An Unprecedented Cyano-Induced Sodium Nitrite-Catalyzed C(sp3)-H and C(sp2)-H Coupling Reaction

2018 ◽  
Vol 15 (7) ◽  
pp. 989-994 ◽  
Author(s):  
Ling Li ◽  
Bo Su ◽  
Yuxiu Liu ◽  
Qingmin Wang
Keyword(s):  
Sodium Nitrite ◽  
Oxidative Coupling ◽  
High Resolution Mass Spectrometry ◽  
Coupling Reaction ◽  
13C Nmr Spectroscopy ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
1H And 13C Nmr ◽  
Oxidative Coupling Reaction ◽  
Oxidative Coupling Reactions

Aim and Objective: During the investigation of sodium nitrite-catalyzed oxidative coupling reaction of aryls, an unprecedented C(sp2)-H and C(sp3)-H coupling of substituted 2-aryl acetonitrile was found. Materials and Methods: The structure of the coupled product was confirmed by 1H and 13C NMR spectroscopy and high-resolution mass spectrometry (HRMS), and comparison of its derivatives with known compounds. The effects of methoxy group in the benzene ring on the reaction were evaluated. Results: The optimized reaction conditions are summarized as follows: CF3SO3H/substrate = 1.5 equiv., NaNO2/substrate = 0.3 equiv., CH3CN as solvent. 2-(4-Methoxyphenyl)acetonitrile and 2-(3,4,5- trimethoxyphenyl)acetonitrile could also generate C(sp2)-H and C(sp3)-H coupling. The coupling reaction occurred as a typical radial mechanism. Conclusion: An unprecedented cyano-induced, NaNO2-catalyzed oxidative C(sp3)-H and C(sp2)-H coupling was reported. The reaction proceeded under very mild conditions, using O2 in the air as terminal oxidant. The unique oxidative manner might provide more inspiration for the development of intriguing oxidative coupling reactions.

Modern Organic Synthesis in the Laboratory

2008 ◽  
Author(s):  
Jie Jack Li ◽  
Chris Limberakis ◽  
Derek A. Pflum
Keyword(s):  
Organic Chemistry ◽  
Graduate Students ◽  
Organic Synthesis ◽  
Functional Group ◽  
Bond Formation ◽  
Reaction Conditions ◽  
Carbon Bond ◽  
Oxidation Reduction ◽  
Carbon Carbon Bond ◽  
Daunting Task

Searching for reaction in organic synthesis has been made much easier in the current age of computer databases. However, the dilemma now is which procedure one selects among the ocean of choices. Especially for novices in the laboratory, it becomes a daunting task to decide what reaction conditions to experiment with first in order to have the best chance of success. This collection intends to serve as an "older and wiser lab-mate" one could have by compiling many of the most commonly used experimental procedures in organic synthesis. With chapters that cover such topics as functional group manipulations, oxidation, reduction, and carbon-carbon bond formation, Modern Organic Synthesis in the Laboratory will be useful for both graduate students and professors in organic chemistry and medicinal chemists in the pharmaceutical and agrochemical industries.

Rh(III)-Catalyzed Olefination and Alkylation of Arenes with Maleimides: A Tunable Strategy for C(sp2)–H Functionalization

Synthesis ◽  
2021 ◽  
Author(s):  
Hongji Li ◽  
Wenjie Zhang ◽  
Xueyan Liu ◽  
Zhenfeng Tian
Keyword(s):  
Room Temperature ◽  
Functional Group ◽  
Reaction Conditions ◽  
Bond Functionalization ◽  
Alkylation Process ◽  
Coupling Partner

AbstractWe herein report a new nitrogen-directed Rh(III)-catalyzed C(sp2)–H bond functionalization of N-nitrosoanilines and azoxybenzenes with maleimides as a coupling partner, in which the olefination/alkylation process can be finely controlled at room temperature by variation of the reaction conditions. This method shows excellent functional group tolerance, and presents a mild access to the resulting olefination/alkylation products in moderate to good yields.

Sulfonyl Radical Triggered Selective Iodosulfonylation and Bicycli-zations of 1,6-Dienes

2021 ◽  
Author(s):  
Shi-Ping Wu ◽  
Dong-Kai Wang ◽  
Qing-Qing Kang ◽  
Guo-Ping Ge ◽  
Hongxing Zheng ◽  
...  
Keyword(s):  
Functional Group ◽  
High Selectivity ◽  
Reaction Conditions ◽  
First Time

A novel sulfonyl radical triggered selective iodosulfonylation and bicyclizations of 1,6-dienes has been described for the first time. High selectivity and efficiency, mild reaction conditions, excellent functional group compatibility, and...

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