Naturally Occuring Organohalogen Compounds — A Comprehensive Survery

Gribble, Gordon W.

doi:10.1007/978-3-7091-6887-5_1

Cited by 50 publications

(35 citation statements)

References 416 publications

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“…All kinetic data therein was consistent with a mechanism involving an irreversible dimer dissociation followed by ligand substitution (P t Bu 3 for P(o-Tol) 3 ) and subsequent reductive elimination (Scheme 63). The use of bulky and electron-rich P t Bu 3 was crucial for this reaction to proceed.…”

Section: Carbon−halogen Reductive Elimination From Pd(ii) Complexessupporting

confidence: 68%

“…Interestingly, after many additives were tested, − NO 3 (functions with numerous counter cations) was found to be crucial. In line with this finding, a highly reactive cationic [Pd(NO 3 )] + generated in situ from nitrate and the Pd precatalyst initiates the C−H bond activation.…”

Section: Carbon−halogen Reductive Elimination From Pd(iv)supporting

confidence: 68%

“…This effect was rationalized by the fact that PEt 3 may be equestered by coordination or alkylation under the reaction conditions. It was also discovered that the same exchange process could occur when the Ni(I) and Ni(0) complex NiBr(PPh 3 ) 3 and Ni(PEt 3 ) 4 were independently employed. However, the efficacy of the alter was thought to be related to a process involving Ni(I) species, which can be formed from ArI oxidative addition to Ni(0) (eq 5).…”

Section: Ni-catalyzed Synthesis Of Aryl Halidesmentioning

confidence: 90%

“…183 This reaction proceeds using Pd 2 (dba) 3 as the Pd(0) precatalyst, and the bulky biarylphosphine t BuBrettPhos as the ligand and both halide analogs can be obtained in excellent yields. Of note was the author's use of PEG3400, i Bu 3 Al, and 2-butanone.…”

Section: Carbon−halogen Reductive Elimination From Pd(ii) Complexesmentioning

confidence: 99%

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Modern Transition-Metal-Catalyzed Carbon–Halogen Bond Formation

2016

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The high utility of halogenated organic compounds has prompted the development of a vast number of transformations which install the carbon-halogen motif. Traditional routes to these building blocks have commonly involved multiple steps, harsh reaction conditions, and the use of stoichiometric and/or toxic reagents. In this regard, using transition metals to catalyze the synthesis of organohalides has become a mature field in itself, and applying these technologies has allowed for a decrease in the production of waste, higher levels of regio- and stereoselectivity, and the ability to produce enantioenriched target compounds. Furthermore, transition metals offer the distinct advantage of possessing a diverse spectrum of mechanistic possibilities which translate to the capability to apply new substrate classes and afford novel and difficult-to-access structures. This Review provides comprehensive coverage of modern transition metal-catalyzed syntheses of organohalides via a diverse array of mechanisms. Attention is given to the seminal stoichiometric organometallic studies which led to the corresponding catalytic processes being realized. By breaking this field down into the synthesis of aryl, vinyl, and alkyl halides, it becomes clear which methods have surfaced as most favored for each individual class. In general, a pronounced shift toward the use of C-H bonds as key functional groups, in addition to methods which proceed by catalytic, radical-based mechanisms has occurred. Although always evolving, this field appears to be heading in the direction of using starting materials with a significantly lower degree of prefunctionalization in addition to less expensive and abundant metal catalysts.

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Section: Carbon−halogen Reductive Elimination From Pd(ii) Complexessupporting

confidence: 68%

Section: Carbon−halogen Reductive Elimination From Pd(iv)supporting

confidence: 68%

Section: Ni-catalyzed Synthesis Of Aryl Halidesmentioning

confidence: 90%

Section: Carbon−halogen Reductive Elimination From Pd(ii) Complexesmentioning

confidence: 99%

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Modern Transition-Metal-Catalyzed Carbon–Halogen Bond Formation

2016

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“…In the meantime, however, many authors have shown that naturally produced organohalogens are neither scarce nor quantitatively negligible. [19][20][21] The lichen/AOX concentrations showed a minimum of 24 mg/kg (town of Kempten), a maximum of 730 mg/kg (city of Hof), and a median value of 90 mg/ kg. While some correlations of high AOX values at localities with high atmospheric pollution (e.g., Hof) and of low AOX values at localities with low metal deposition occur, a systematic correlation could not be found between these two independent variable groups.…”

Section: Do Lichen Reflect Atmospheric Depositions?mentioning

confidence: 99%

Epilithic Lichen—Atmospheric Deposition Monitors of Trace Elements and Organohalogens?

Matschullat

Scharnweber²,

Garbe‐Schönberg³

et al. 1999

Journal of the Air & Waste Management Association

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Epilithic lichen (Xanthoria elegans in Canada, Lecanora muralis in Germany) were gathered from 17 locations in Ontario, Canada (from Lake Ontario to James Bay) and 43 locations in Germany (from the Alps to the North Sea and from the Baltic Sea to the Erzgebirge). Sample aliquots were digested in nitric acid and trace elements were analyzed by inductively coupled plasma-mass spectrometry techniques. The organohalogens were determined IMPLICATIONSThe results demonstrate that epilithic lichen provide an excellent means to monitor atmospheric deposition over large areas in a fast, simple, cost-effective, and reliable way. This method is fast because lichen specimens can be easily sampled and are abundant in all environmentsprovided that suitable species (i.e., those that are easily determinable and ubiquitous) have been chosen. This method is inexpensive when compared to instrumental methods of measuring atmospheric depositions, which will never be set up in densities comparable to the use of biomonitors. The method is thus very attractive for regions where no high-tech monitoring facilities exist and where large areas will be covered in a short period of time. Finally, the reliability of the method can be shown by comparing the results of this study with those of other types of biomonitoring and direct measurements. This method is expected to extend the spatial resolution and to produce a lichen-based biogeochemical atlas for Germany.as absorbable organic halogens (AOXs) by coulometry. Concentration ranges from Germany for trace element samples and AOXs were determined. The lichen showed high spatial resolution in their element enrichment patterns. This allowed for differentiation between natural and anthropogenic dominance in ambient air concentrations. This biomonitoring method has proven to be very sensitive, fast, and reliable. No clear relationship could be found between trace element and AOX concentrations. The AOX values may reflect individual metabolic rates of the fungal partner in lichen symbionts.

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Chloride and Organic Chlorine in Soil

Öberg¹

1998

Acta hydrochim. hydrobiol.

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Naturally Occuring Organohalogen Compounds — A Comprehensive Survery

Cited by 50 publications

References 416 publications

Modern Transition-Metal-Catalyzed Carbon–Halogen Bond Formation

Modern Transition-Metal-Catalyzed Carbon–Halogen Bond Formation

Epilithic Lichen—Atmospheric Deposition Monitors of Trace Elements and Organohalogens?

Chloride and Organic Chlorine in Soil

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