Mild metal-catalyzed C–H activation: examples and concepts

Chemical Society Reviews, Journal Year: 2016, Volume and Issue: 45(10), P. 2900 - 2936

Published: Jan. 1, 2016

C–H Activation reactions that proceed under mild conditions are more attractive for applications in complex molecule synthesis. Mild transformations reported since 2011 reviewed and the different concepts strategies have enabled their mildness discussed.

Language: Английский

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A comprehensive overview of directing groups applied in metal-catalysed C–H functionalisation chemistry

Chemical Society Reviews, Journal Year: 2018, Volume and Issue: 47(17), P. 6603 - 6743

Published: Jan. 1, 2018

The present review is devoted to summarizing the recent advances (2015-2017) in field of metal-catalysed group-directed C-H functionalisation. In order clearly showcase molecular diversity that can now be accessed by means directed functionalisation, whole organized following directing groups installed on a substrate. Its aim comprehensive reference work, where specific group easily found, together with transformations which have been carried out it. Hence, primary format this schemes accompanied concise explanatory text, are ordered sections according their chemical structure. feature typical substrates used, products obtained as well required reaction conditions. Importantly, each example commented respect most important positive features and drawbacks, aspects such selectivity, substrate scope, conditions, removal, greenness. targeted readership both experts functionalisation chemistry (to provide overview progress made last years) and, even more so, all organic chemists who want introduce way thinking for design straightforward, efficient step-economic synthetic routes towards molecules interest them. Accordingly, should particular also scientists from industrial R&D sector. overall goal promote application reactions outside research dedicated method development establishing it valuable archetype contemporary R&D, comparable role cross-coupling play date.

Language: Английский

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Iron-Catalyzed C–H Bond Activation

Chemical Reviews, Journal Year: 2017, Volume and Issue: 117(13), P. 9086 - 9139

Published: April 5, 2017

Catalytic C-H bond activation, which was an elusive subject of chemical research until the 1990s, has now become a standard synthetic method for formation new C-C and C-heteroatom bonds. The potential activation first described ruthenium catalysis is widely exploited by use various precious metals. Driven increasing interest in utilization ubiquitous metals that are abundant nontoxic, iron rapidly growing area research, iron-catalyzed been most actively explored recent years. In this review, we summarize development stoichiometric long history, catalytic functionalization, emerged about 10 years ago. We focus review on reactions take place via reactive organoiron intermediates, excluded those as Lewis acid or radical initiator. contents categorized type cleaved formed thereafter, it covers simple substrates possessing directing group anchors catalyst to substrate, providing overview iron-mediated reported literature October 2016.

Language: Английский

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

ACS Central Science, Journal Year: 2016, Volume and Issue: 2(5), P. 281 - 292

Published: May 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.

Language: Английский

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Evolution of C–H Bond Functionalization from Methane to Methodology

Journal of the American Chemical Society, Journal Year: 2015, Volume and Issue: 138(1), P. 2 - 24

Published: Nov. 13, 2015

This Perspective presents the fundamental principles, elementary reactions, initial catalytic systems, and contemporary catalysts that have converted C–H bond functionalization from a curiosity to reality for synthetic chemists. Many classes of reactions involving transition-metal complexes cleave bonds at typically unreactive positions. These coupled with separate or simultaneous process lead products containing new C–C, C–N, C–O bonds. Such were initially studied conversion light alkanes liquid products, but they been used (and commercialized in some cases) most often synthesis more complex structures natural medicinally active compounds, aromatic materials. change direction research is remarkable because must occur an unactivated over functional groups are reactive than toward classical reagents. The scope form C–C install functionality will be presented, potential future utility these discussed.

Language: Английский

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Transition-Metal-Catalyzed Cleavage of C–N Single Bonds

Chemical Reviews, Journal Year: 2015, Volume and Issue: 115(21), P. 12045 - 12090

Published: Oct. 1, 2015

ADVERTISEMENT RETURN TO ISSUEPREVReviewTransition-Metal-Catalyzed Cleavage of C–N Single BondsKunbing Ouyang†‡, Wei Hao†, Wen-Xiong Zhang*†§, and Zhenfeng Xi†View Author Information† Beijing National Laboratory for Molecular Sciences (BNLMS), Key Bioorganic Chemistry Engineering the Ministry Education, College Chemistry, Peking University, 100871, China‡ Institute Chinese Academy (CAS), 100190, China§ State Elemento-Organic Nankai Tianjin 300071, China*E-mail: [email protected]Cite this: Chem. Rev. 2015, 115, 21, 12045–12090Publication Date (Web):October 1, 2015Publication History Received3 July 2015Published online1 October inissue 11 November 2015https://pubs.acs.org/doi/10.1021/acs.chemrev.5b00386https://doi.org/10.1021/acs.chemrev.5b00386review-articleACS PublicationsCopyright © 2015 American Chemical SocietyRequest reuse permissionsArticle Views26285Altmetric-Citations562LEARN ABOUT THESE METRICSArticle Views are COUNTER-compliant sum full text article downloads since 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 given article. how calculated. Share Add toView InAdd Full Text ReferenceAdd Description ExportRISCitationCitation abstractCitation referencesMore Options onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose SUBJECTS:Amines,Bond cleavage,Cations,Oxidative addition,Salts Get e-Alerts

Language: Английский

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Transition metal-catalyzed site- and regio-divergent C–H bond functionalization

Chemical Society Reviews, Journal Year: 2017, Volume and Issue: 46(14), P. 4299 - 4328

Published: Jan. 1, 2017

The regioselectivity of C–H functionalization reactions can be redirected to obtain regioisomeric products form the same starting materials.

Language: Английский

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Simple Amine-Directed Meta-Selective C–H Arylation via Pd/Norbornene Catalysis

Journal of the American Chemical Society, Journal Year: 2015, Volume and Issue: 137(18), P. 5887 - 5890

Published: April 24, 2015

Herein we report a highly meta-selective C–H arylation using simple tertiary amines as the directing group. This method takes advantage of Pd/norbornene catalysis, offering distinct strategy to control site selectivity. The reaction was promoted by commercially available AsPh3 ligand and unique "acetate cocktail". Aryl iodides with an ortho electron-withdrawing group were employed coupling partner. A wide range functional groups, including some heteroarenes, are tolerated under conditions. In addition, amine can be easily installed transformed other common versatile groups. We expect this functionalization mode have broad implications for developing transformations beyond work.

Language: Английский

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Recent Advances in Transition-Metal-Catalyzed Synthetic Transformations of Organosilicon Reagents

ACS Catalysis, Journal Year: 2016, Volume and Issue: 7(1), P. 631 - 651

Published: Dec. 2, 2016

Organosilicon compounds act as a nucleophile upon activation by an appropriate base and behave in manner similar to main-group organometallic reagents. In the last decades, structurally divergent organosilicon reagents are available have become more employed for synthetic transformation with aid of transition-metal complexes, because general superior other view stability, solubility, nontoxicity, easy-handling. Particularly, cross-coupling organic halides or pseudohalides has been considered be useful tool constructing carbon frameworks various target molecules such pharmaceuticals π-conjugated functional materials. Perfluoroalkylsilicon CF3SiEt3 found use metal-catalyzed introduction perfluoroalkyl groups into many substrates. addition, functionalized readily accessible catalytic approach starting hydrocarbons alkenes, alkynes, alkanes, arenes. This article reviews recent advances transition-metal-catalyzed transformations according type metal catalyst.

Language: Английский

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Dehydrogenation of Alkanes and Aliphatic Groups by Pincer-Ligated Metal Complexes

Chemical Reviews, Journal Year: 2017, Volume and Issue: 117(19), P. 12357 - 12384

Published: Sept. 27, 2017

The alkyl group is the most common component of organic molecules and difficult to selectively functionalize. development catalysts for dehydrogenation groups give corresponding olefins could open almost unlimited avenues functionalization. Homogeneous systems, or more generally systems based on molecular (including solid-supported) catalysts, probably offer greatest potential regio- chemoselective alkanes. progress date in this area has been achieved with pincer-ligated transition-metal-based catalysts; related chemistry are subject review. Chemists still far from achieving obvious perhaps attractive goal area, simple alkanes yield alkenes (specifically monoenes) high selectivity. Greater made tandem catalysis approaches which initial dehydrogenated product undergoes a desirable secondary reaction. Also reviewed substantial that closely substrates containing heteroatoms.

Language: Английский

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