Factor F430-Like Catalysis of Ni(tmtaa) (tmtaa = Dianion of 6,8,15,17-Tetramethyl-5,14-dihydrodibenzo[b,i][1,4,8,11]tetraazacyclotetradecine) for Reductive Dehalogenation of Alkyl Halides

1994 ◽  
Vol 67 (3) ◽  
pp. 705-709 ◽  
Author(s):  
Toru Arai ◽  
Kimio Kashitani ◽  
Hiroshi Kondo ◽  
Shigeyoshi Sakaki
Keyword(s):  
Alkyl Halides ◽  
Reductive Dehalogenation ◽  
Factor F430

Visible-light-mediated hydrodehalogenation and Br/D exchange of inactivated aryl and alkyl halides with a palladium complex

2019 ◽  
Vol 6 (10) ◽  
pp. 1649-1654 ◽  
Author(s):  
Zhao-Zhao Zhou ◽  
Jia-Hui Zhao ◽  
Xue-Ya Gou ◽  
Xi-Meng Chen ◽  
Yong-Min Liang
Keyword(s):  
Visible Light ◽  
Palladium Complex ◽  
Radical Addition ◽  
Alkyl Halides ◽  
Reductive Dehalogenation ◽  
Reductive Cyclization ◽  
Alkyl Bromides

Photo-induced radical reductive dehalogenation of inactivated aryl/alkyl bromides and chlorides with a palladium complex is described. Reductive cyclization, dehalogenative deuteration, and radical addition process can be achieved smoothly.

Vitamin B12-based elimination of alkyl halides

2020 ◽  
Author(s):  
Julian West ◽  
Alexandros S Pollatos ◽  
Radha Bam
Keyword(s):  
Vitamin B12 ◽  
Alkyl Halides

Fe-Catalyzed Conjunctive Cross-Couplings of Unactivated Alkenes with Grignard Reagents

2020 ◽  
Author(s):  
Lei Liu ◽  
Wes Lee ◽  
Cassandra R. Youshaw ◽  
Mingbin Yuan ◽  
Michael B. Geherty ◽  
...  
Keyword(s):  
Functional Groups ◽  
Cross Coupling ◽  
Alkyl Halides ◽  
Grignard Reagents ◽  
Turnover Frequency ◽  
Diverse Range ◽  
Cascade Cyclization ◽  
Radical Cascade

The first iron-catalyzed three-component cross-coupling of unactivated olefins with alkyl halides and Grignard reagents is reported. The reaction operates under fast turnover frequency and tolerates a diverse range of sp2-hybridized nucleophiles, alkyl halides, and unactivated olefins bearing diverse functional groups to yield the desired 1,2-alkylarylated products with high regiocontrol. Further, we demonstrate that this protocol is amenable for the synthesis of new (hetero)carbocycles including tetrahydrofurans and pyrrolidines via a three-component radical cascade cyclization/arylation that forges three new C-C bonds.

Design and Development of Fe-Catalyzed Intra- and Intermolecular Carbofunctionalization of Vinyl Cyclopropanes

2019 ◽  
Author(s):  
Lei Liu ◽  
Wes Lee ◽  
Mingbin Yuan ◽  
Chris Acha ◽  
Michael B. Geherty ◽  
...  
Keyword(s):  
Bond Formation ◽  
Cross Coupling ◽  
Alkyl Halides ◽  
Grignard Reagents ◽  
Mechanistic Studies ◽  
Radical Intermediates ◽  
Design And Implementation ◽  
Solvent Cage ◽  
Radical Cascade ◽  
Radical Processes

Design and implementation of the first (asymmetric) Fe-catalyzed intra- and intermolecular difunctionalization of vinyl cyclopropanes (VCPs) with alkyl halides and aryl Grignard reagents has been realized via a mechanistically driven approach. Mechanistic studies support the diffusion of the alkyl radical intermediates out of the solvent cage to participate in an intra- or -intermolecular radical cascade with the VCP followed by re-entering the Fe radical cross-coupling cycle to undergo selective C(sp2)-C(sp3) bond formation. Overall, we provide new design principles for Fe-mediated radical processes and underscore the potential of using combined computations and experiments to accelerate the development of challenging transformations.

Reductive Dehalogenation of Environmental Contaminants: A Critical Review

1989 ◽  
Vol 24 (2) ◽  
pp. 299-322 ◽  
Author(s):  
R. M. Baxter
Keyword(s):  
Hydrogen Atom ◽  
Aromatic Compounds ◽  
Reductive Dechlorination ◽  
Halogen Atom ◽  
Environmental Contaminants ◽  
Methanogenic Bacteria ◽  
Photochemical Reactions ◽  
Reductive Dehalogenation ◽  
Iron Porphyrins ◽  
Aliphatic Compounds

Abstract It is generally recognized that reductive processes are more important than oxidative ones in transforming, degrading and mineralizing many environmental contaminants. One process of particular importance is reductive dehalogenation, i.e., the replacement of a halogen atom (most commonly a chlorine atom) by a hydrogen atom. A number of different mechanisms are involved in these reactions. Photochemical reactions probably play a role in some instances. Aliphatic compounds such as chloroethanes, partly aliphatic compounds such as DDT, and alicyclic compounds such as hexachlorocyclohexane are readily dechlorinated in the laboratory by reaction with reduced iron porphyrins such as hematin. Many of these are also dechlorinated by cultures of certain microorganisms, probably by the same mechanism. Such compounds, with a few exceptions, have been found to undergo reductive dechlorination in the environment. Aromatic compounds such as halobenzenes, halophenols and halobenzoic acids appear not to react with reduced iron porphyrins. Some of these however undergo reductive dechlorination both in the environment and in the laboratory. The reaction is generally associated with methanogenic bacteria. There is evidence for the existence of a number of different dechlorinating enzymes specific for different isomers. Recently it has been found that many components of polychlorinated biphenyls (PCBs), long considered to be virtually totally resistant to environmental degradation, may be reductively dechlorinated both in the laboratory and in nature. These findings suggest that many environmental contaminants may prove to be less persistent than was previously feared.

Biotreatability test of bleach wastewaters from pulp and paper mills

1997 ◽  
Vol 35 (2-3) ◽  
pp. 101-108
Author(s):  
X. Wang ◽  
T. H. Mize ◽  
F. M. Saunders ◽  
S. A. Baker
Keyword(s):  
Wastewater Treatment ◽  
Pulp And Paper ◽  
Reductive Dehalogenation ◽  
Continuous Reactor ◽  
Batch Reactors ◽  
Aerobic Treatment ◽  
Pulp And Paper Mills ◽  
Paper Mills ◽  
Degradation Rates ◽  
Adsorbable Organic Halide

Research is focused on an integrated way to simultaneously optimize the bleaching operations and subsequent wastewater treatment for pulp and paper mills. Bleach wastewaters from ClO2-bleached pulping studies at Institute of Paper Science and Technology (IPST) were used as the feed for batch reactors to test and rank the treatability and kinetics. The key aspect of the system is the use of sequential anaerobic/aerobic phases to enhance reductive dehalogenation of chloro-organic materials. Two continuous reactor systems, one operated in an anaerobic-aerobic mode and a second in an aerobic-aerobic mode, received bleaching wastewater obtained from a full-scale plant. Acclimated cultures from both continuous reactors were used to quantify the AOX (Adsorbable Organic Halide) and COD removal from various bleaching wastewaters. In general, the sequential anaerobic/aerobic treatment of bleach wastewater can improve both biotreatability and degradation rates.

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