Palladium-Catalyzed Ligand-Directed C−H Functionalization Reactions

Chemical Reviews, Год журнала: 2010, Номер 110(2), С. 1147 - 1169

Опубликована: Янв. 15, 2010

ADVERTISEMENT RETURN TO ISSUEPREVReviewNEXTPalladium-Catalyzed Ligand-Directed C−H Functionalization ReactionsThomas W. Lyons and Melanie S. Sanford*View Author Information Department of Chemistry, University Michigan, 930 North Avenue, Ann Arbor, Michigan 48109* To whom correspondence should be addressed. E-mail: [email protected]Cite this: Chem. Rev. 2010, 110, 2, 1147–1169Publication Date (Web):January 15, 2010Publication History Received8 May 2009Published online15 January 2010Published inissue 10 February 2010https://pubs.acs.org/doi/10.1021/cr900184ehttps://doi.org/10.1021/cr900184ereview-articleACS PublicationsCopyright © 2010 American Chemical SocietyRequest reuse permissionsArticle Views81864Altmetric-Citations5606LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum full text article downloads since November 2008 (both PDF HTML) across all institutions individuals. These metrics regularly updated to reflect usage leading up last few days.Citations number other articles citing this article, calculated by Crossref daily. Find more information about citation counts.The Altmetric Attention Score is a quantitative measure attention that research has received online. Clicking on donut icon will load page at altmetric.com with additional details score social media presence for given article. how calculated. Share Add toView InAdd Full Text ReferenceAdd Description ExportRISCitationCitation abstractCitation referencesMore Options onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose SUBJECTS:Chemical reactions,Functionalization,Halogenation,Palladium,Reagents Get e-Alerts

Язык: Английский

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Rhodium-Catalyzed C−C Bond Formation via Heteroatom-Directed C−H Bond Activation

Chemical Reviews, Год журнала: 2009, Номер 110(2), С. 624 - 655

Опубликована: Май 13, 2009

ADVERTISEMENT RETURN TO ISSUEPREVReviewNEXTRhodium-Catalyzed C−C Bond Formation via Heteroatom-Directed C−H ActivationDenise A. Colby, Robert G. Bergman*, and Jonathan Ellman*View Author Information Department of Chemistry, University California, Division Chemical Sciences, Lawrence Berkeley National Laboratory, Berkeley, 94720* E-mail: [email protected] protected]Cite this: Chem. Rev. 2010, 110, 2, 624–655Publication Date (Web):May 13, 2009Publication History Received7 January 2009Published online13 May inissue 10 February 2010https://pubs.acs.org/doi/10.1021/cr900005nhttps://doi.org/10.1021/cr900005nreview-articleACS PublicationsCopyright © 2009 American SocietyRequest reuse permissionsArticle Views44444Altmetric-Citations3479LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum full text article downloads since November 2008 (both PDF HTML) across all institutions individuals. These metrics regularly updated to reflect usage leading up last few days.Citations number other articles citing this article, calculated by Crossref daily. Find more information about citation counts.The Altmetric Attention Score is a quantitative measure attention that research has received online. Clicking on donut icon will load page at altmetric.com with additional details score social media presence for given article. how calculated. Share Add toView InAdd Full Text ReferenceAdd Description ExportRISCitationCitation abstractCitation referencesMore Options onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose SUBJECTS:Alcohols,Arylation,Catalysts,Hydrocarbons,Post-translational modification Get e-Alerts

Язык: Английский

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The microbial nitrogen-cycling network

Nature Reviews Microbiology, Год журнала: 2018, Номер 16(5), С. 263 - 276

Опубликована: Фев. 5, 2018

Язык: Английский

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Weak Coordination as a Powerful Means for Developing Broadly Useful C–H Functionalization Reactions

Accounts of Chemical Research, Год журнала: 2011, Номер 45(6), С. 788 - 802

Опубликована: Дек. 14, 2011

Reactions that convert carbon–hydrogen (C–H) bonds into carbon–carbon (C–C) or carbon–heteroatom (C–Y) are attractive tools for organic chemists, potentially expediting the synthesis of target molecules through new disconnections in retrosynthetic analysis. Despite extensive inorganic and organometallic study insertion homogeneous metal species unactivated C–H bonds, practical applications this technology chemistry still rare. Only past decade have metal-catalyzed functionalization reactions become more widely utilized synthesis.Research area transition metal–catalyzed can be broadly grouped two subfields. They reflect different approaches goals thus challenges opportunities. One approach involves completely unfunctionalized aromatic aliphatic hydrocarbons, which we refer to as "first functionalization". Here substrates nonpolar hydrophobic interact very weakly with polar species. To overcome weak affinity drive metal-mediated cleavage, chemists often use hydrocarbon large excess (for example, solvent). Because highly reactive needed first functionalization, controlling chemoselectivity avoid overfunctionalization is difficult. Additionally, because both products comparatively low-value chemicals, developing cost-effective catalysts exceptionally high turnover numbers competitive alternatives (including heterogeneous catalysts) challenging. Although an exciting field, beyond scope Account.The second subfield containing one pre-existing functional groups, termed "further advantage existing group (or groups) used chelate catalyst position it selective cleavage. Precoordination paraffin nature by increasing effective concentration substrate so need not solvent. From a synthetic perspective, desirable intrinsic part extra steps installation removal external directing avoided. In way, dramatic increases molecular complexity accomplished single stroke stereo- site-selective introduction group. reactivity major challenge (as functionalization), philosophy further differs; work predictable selectivity intricately functionalized contexts on commonly occurring structural motifs.In Account, focus emergent theme within literature: groups direct cleavage coordination. We discuss our motivation studying Pd-catalyzed assisted coordinating chronicle endeavors bring type fruition. Through approach, developed diverse range coupling partners, broad likely stemming from cyclopalladated intermediates, held together interactions.

Язык: Английский

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Catalytic C–H functionalization by metal carbenoid and nitrenoid insertion

Nature, Год журнала: 2008, Номер 451(7177), С. 417 - 424

Опубликована: Янв. 1, 2008

Язык: Английский

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Palladium-Catalyzed Transformations of Alkyl C–H Bonds

Chemical Reviews, Год журнала: 2016, Номер 117(13), С. 8754 - 8786

Опубликована: Дек. 2, 2016

This Review summarizes the advancements in Pd-catalyzed C(sp3)-H activation via various redox manifolds, including Pd(0)/Pd(II), Pd(II)/Pd(IV), and Pd(II)/Pd(0). While few examples have been reported of alkane C-H bonds, many activation/C-C C-heteroatom bond forming reactions developed by use directing group strategies to control regioselectivity build structural patterns for synthetic chemistry. A number mono- bidentate ligands also proven be effective accelerating directed weakly coordinating auxiliaries, which provides great opportunities reactivity selectivity (including enantioselectivity) functionalization reactions.

Язык: Английский

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Recent Advances in Petroleum Microbiology

Microbiology and Molecular Biology Reviews, Год журнала: 2003, Номер 67(4), С. 503 - 549

Опубликована: Дек. 1, 2003

Recent advances in molecular biology have extended our understanding of the metabolic processes related to microbial transformation petroleum hydrocarbons. The physiological responses microorganisms presence hydrocarbons, including cell surface alterations and adaptive mechanisms for uptake efflux these substrates, been characterized. New techniques enhanced ability investigate dynamics communities petroleum-impacted ecosystems. By establishing conditions which maximize rates extents growth, hydrocarbon access, transformation, highly accelerated bioreactor-based waste degradation implemented. Biofilters capable removing biodegrading volatile contaminants air streams with short substrate-microbe contact times (<60 s) are being used effectively. Microbes injected into partially spent reservoirs enhance oil recovery. However, not exhibited consistent effective performance, primarily because inability control subsurface environment. may be exploited break stable oilfield emulsions produce pipeline quality oil. There is interest replacing physical desulfurization biodesulfurization methods through promotion selective sulfur removal without associated carbon moieties. since microbes require an environment containing some water, a two-phase oil-water system must established optimize between hydrocarbon, such emulsion easily created viscous crude This challenge circumvented by application technology more refined gasoline diesel where aqueous-hydrocarbon generated. Molecular approaches broaden substrate specificity increase desulfurization. Bacterial commercialized H(2)S sulfoxides from petrochemical streams. also potential use nitrogen leading reduced nitric oxide emissions provided that technical problems similar those experienced can solved. Enzymes added-value products bacterial biosensors analyze petroleum-contaminated environments.

Язык: Английский

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Carbon–heteroatom bond formation catalysed by organometallic complexes

Nature, Год журнала: 2008, Номер 455(7211), С. 314 - 322

Опубликована: Сен. 17, 2008

Язык: Английский

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Undirected, Homogeneous C–H Bond Functionalization: Challenges and Opportunities

ACS Central Science, Год журнала: 2016, Номер 2(5), С. 281 - 292

Опубликована: Май 2, 2016

The functionalization of C–H bonds has created new approaches to preparing organic molecules by enabling strategic "disconnections" during the planning a synthetic route. Such functionalizations also have ability derivatize complex modifying one or more many bonds. For these reasons, researchers are developing types reactions and applications processes. These bond can be divided into two general classes: those directed coordination an existing functional group prior cleavage (directed) occurring without (undirected). undirected much less common challenging develop than reactions. This outlook will focus on functionalization, as well related that occur noncovalent association catalyst cleavage. inherent challenges conducting methods for being developed presented, along with factors govern selectivity in Finally, this discusses future directions research emphasis limitations must overcome if type methodology is become widely used academia industry.

Язык: Английский

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Single-site trinuclear copper oxygen clusters in mordenite for selective conversion of methane to methanol

Nature Communications, Год журнала: 2015, Номер 6(1)

Опубликована: Июнь 25, 2015

Abstract Copper-exchanged zeolites with mordenite structure mimic the nuclearity and reactivity of active sites in particulate methane monooxygenase, which are enzymes able to selectively oxidize methanol. Here we show that micropores provide a perfect confined environment for highly selective stabilization trinuclear copper-oxo clusters exhibit high towards activation carbon–hydrogen bonds its subsequent transformation The similarity enzymatic systems is also implied from reversible rearrangements occurring during transformations along reaction path methanol, both enzyme system copper-exchanged mordenite.

Язык: Английский

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