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 One-Step Synthesis of Acylboron Compounds via Cu-Catalyzed Carbonylative Borylation of Alkyl Halides

2020 ◽  
Author(s):  
Cheng Li-Jie ◽  
Zhao Siling ◽  
Neal Mankad
Keyword(s):  
Alkyl Halides ◽  
Efficient Synthesis ◽  
Mechanistic Studies ◽  
Acyl Halide ◽  
Reaction Conditions ◽  
One Pot ◽  
One Step ◽  
High Yields ◽  
Tertiary Alkyl

A Cu-catalyzed carbonylative borylation of unactivated alkyl halides has been developed, enabling efficient synthesis of aliphatic potassium acyltrifluoroborates (KATs) in high yields by treating the in-situ formed tetracoordinated acylboron intermediates with aqueous KHF2. A variety of functional groups are tolerated under the mild reaction conditions, and primary, secondary and tertiary alkyl halides are all applicable. In addition, this method also provides facile access to N-methyliminodiacetyl (MIDA) acylboronates as well as α-methylated potassium acyltrifluoroborates in a one-pot manner. Mechanistic studies indicate a radical atom transfer carbonylation (ATC) mechanism to form acyl halide intermediates that are subsequently borylated by (NHC)CuBpin.<br>

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.

Palladium-catalyzed Suzuki cross-couplings of N′-mesyl arylhydrazines via C–N bond cleavage

RSC Advances ◽  
2014 ◽  
Vol 4 (49) ◽  
pp. 25576-25579 ◽  
Author(s):  
He-Ping Zhou ◽  
Jin-Biao Liu ◽  
Jian-Jun Yuan ◽  
Yi-Yuan Peng
Keyword(s):  
Boronic Acid ◽  
Bond Cleavage ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Mild Conditions ◽  
Cross Coupling Reaction ◽  
Palladium Catalyzed ◽  
High Yields ◽  
Aryl Boronic Acid ◽  
Biaryl Compounds

An efficient palladium-catalyzed Suzuki cross-coupling reaction of N′-mesyl arylhydrazine with aryl boronic acid is described, which affords the corresponding biaryl compounds in high yields. This transformation proceeds through C–N bond cleavage under mild conditions.

Synthesis of Phenylferrocene in Supercritical Carbon Dioxide

2012 ◽  
Vol 550-553 ◽  
pp. 639-642
Author(s):  
Fawang Li ◽  
Quan Ling Suo ◽  
Hai Long Hong ◽  
Li Min Han
Keyword(s):  
Carbon Dioxide ◽  
Polyethylene Glycol ◽  
Organic Solvent ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Environmentally Benign ◽  
Reaction Conditions ◽  
Cross Coupling Reaction ◽  
Ligand Free ◽  
Phenylboronic Acids

The environmentally benign Suzuki cross-coupling reaction was developed by using ScCO2(Supercritical CO2) instead of traditionally organic solvent. In the paper the compound phenylferrocene was synthesized by the Suzuki cross-coupling reaction of iodoferrocene and phenylboronic acids in ScCO2/PEG (polyethylene glycol) with excellent yield ratio in the presence of ligand-free Pd/C catalyst and K2CO3.1.5H2O as base. The Pd/C catalyst can be reused by simply washing sequence and CO2can be recycled after depressurization. The catalytic reaction conditions were optimized in the reaction using ScCO2as solvent.

Enhanced catalytic performance of Pd–Pt nanodendrites for ligand-free Suzuki cross-coupling reactions

RSC Advances ◽  
2015 ◽  
Vol 5 (36) ◽  
pp. 28467-28473 ◽  
Author(s):  
Zheng-Jun Wang ◽  
Jing-Jing Lv ◽  
Jiu-Ju Feng ◽  
Ningbo Li ◽  
Xinhua Xu ◽  
...  
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Catalytic Performance ◽  
Coupling Reactions ◽  
Wet Chemical Method ◽  
One Pot ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Ligand Free ◽  
Wet Chemical

The Pd–Pt NDs were synthesized by a one-pot wet-chemical method, which showed enhanced catalytic activity toward Suzuki cross-coupling reaction.

Efficient ligand-free Hiyama cross-coupling reaction catalyzed by functionalized SBA-15-supported Pd nanoparticles

2014 ◽  
Vol 16 (5) ◽  
pp. 2706-2712 ◽  
Author(s):  
Shao-Hsien Huang ◽  
Chun-Hsia Liu ◽  
Chia-Min Yang
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Pd Nanoparticles ◽  
Reaction Conditions ◽  
Pd Catalysts ◽  
Cross Coupling Reaction ◽  
Supported Pd Catalysts ◽  
Ligand Free ◽  
Recyclable Catalysts ◽  
Supported Pd

Functionalized SBA-15-supported Pd catalysts were prepared as efficient and recyclable catalysts for ligand-free Hiyama cross-coupling under relatively mild reaction conditions.

Synthesis of Internal Alkynes through an Effective Tandem ­Elimination–Hydrodebromination–Cross-Coupling of gem-­Dibromoalkenes with Halobenzenes

Synlett ◽  
2017 ◽  
Vol 29 (02) ◽  
pp. 209-214 ◽  
Author(s):  
Yuan Ji ◽  
Ning Zhong ◽  
Zinan Kang ◽  
Guobing Yan ◽  
Ming Zhao
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Sonogashira Coupling ◽  
Reaction Conditions ◽  
One Pot ◽  
Cross Coupling Reaction ◽  
Sonogashira Coupling Reaction ◽  
Palladium Catalyzed ◽  
Internal Alkyne

Carbon–carbon couplings are among the most important strategies for constructing functional molecules in organic synthetic chemistry, and cheap, diverse, and readily available coupling partners are crucial to these diverse reactions. In this contribution, we report the first palladium-catalyzed C–C cross-coupling reaction of two kinds of organic halide, a gem-dibromoalkene and a halobenzene, as the starting materials. Terminal alkynes were generated in situ through a tandem elimination–hydrodebromination process, and the internal alkyne final products were synthesized in one pot. The reaction proceeded under simple, facile, and classic copper-free Sonogashira coupling reaction conditions in good to excellent yields.

On direct iron-catalyzed cross-coupling reactions

2010 ◽  
Vol 82 (7) ◽  
pp. 1545-1553 ◽  
Author(s):  
Waldemar Maximilian Czaplik ◽  
Matthias Mayer ◽  
Sabine Grupe ◽  
Axel Jacobi von Wangelin
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Alkyl Halides ◽  
Coupling Reactions ◽  
One Pot ◽  
Iron Catalysis ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Direct Cross

A new methodology for the direct cross-coupling reaction between aryl halides and alkyl halides under iron catalysis is described. Unlike conventional protocols, the direct cross-coupling obviates the need for the preformation of stoichiometric amounts of Grignard species and thus exhibits a reduced hazard potential. The underlying one-pot reaction involves iron-catalyzed Grignard formation followed by a rapid cross-coupling step. Mechanistic data on the role of N,N,N',N'-tetramethylethylenediamine (TMEDA) as additive, the concentration of intermediates, and the nature of the catalyst species are discussed.

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