scholarly journals Recent Advances in Nickel Catalysis Enabled by Stoichiometric Metallic Reducing Agents

Synthesis ◽  
2017 ◽  
Vol 50 (03) ◽  
pp. 499-513 ◽  
Author(s):  
Edward Richmond ◽  
Joseph Moran
Keyword(s):  
Cross Coupling ◽  
Short Review ◽  
Reducing Agents ◽  
Nickel Catalysis ◽  
Future Directions ◽  
Recent Advances ◽  
Reductive Carboxylation

This short review describes recent advances in the field of nickel catalysis, specifically transformations employing stable Ni(II) precatalysts that are activated in situ with the use of stoichiometric metallic reducing agents. The article seeks to summarise the field, highlighting key studies and discussing mechanistic facets. The review closes with an eye on future directions in redox-enabled nickel catalysis.1 Introduction2 Nickel Catalysis Enabled by Metallic Reducing Agents3 Reductive Cross-Coupling4 Reductive Carboxylation and Acylation-type reactions5 Miscellaneous Reactivity6 Perspectives and Future Directions

Recent Advances in Metal-Catalyzed, Electrochemical Coupling Reactions of sp2 Halides/Boronic Acids and sp3 Centers

Synthesis ◽  
2020 ◽  
Author(s):  
Zachary J. Gale-Day
Keyword(s):  
Cross Coupling ◽  
Short Review ◽  
Boronic Acids ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Organic Electrochemistry ◽  
Recent Advances ◽  
Electrochemical Coupling ◽  
Metal Catalyzed

AbstractTraditionally, metal-catalyzed cross-coupling reactions rely on stable but expensive metals, such as palladium. However, the recent development of synthetic organic electrochemistry allows for in situ redox manipulations, expanding the use of cheaper, abundant and sustainable metals, such as nickel and copper as efficient cross-coupling catalysts. This short review covers the recent advances in metal-catalyzed electrochemical coupling reactions, with a focus on reactions of sp2 electrophiles and nucleophiles with sp3 coupling partners to form both C–C and C–heteroatom bonds.1 Introduction2 Nickel-Catalyzed C–C sp2–sp3 Coupling Reactions3 Coupling of Aryl Groups with Heteroatomic Nuclei4 Conclusion

Recent Advances of 1,3,5-Triazinanes in Aminomethylation and Cycloaddition Reactions

Synthesis ◽  
2020 ◽  
Vol 52 (17) ◽  
pp. 2469-2482
Author(s):  
Jia-Rong Chen ◽  
Dong Liang ◽  
Wen-Jing Xiao
Keyword(s):  
Reaction Mechanisms ◽  
Short Review ◽  
Cycloaddition Reactions ◽  
Recent Advances ◽  
Nitrogen Containing Compounds

1,3,5-Trisubstituted 1,3,5-triazinanes (hexahydro-1,3,5-triazines), as stable and readily available surrogates for formaldimines, have found extensive applications for the construction of various nitrogen-containing compounds. The formaldimines, formed in situ from this reagent class, can participate in various aminomethylation and cycloaddition­ reactions. This short review presents recent advances in this field with emphasis on the conceptual ideas behind the developed methodologies and the reaction mechanisms.1 Introduction2 Aminomethylations with 1,3,5-Triazinanes3 Cycloadditions with 1,3,5-Triazinanes3.1 Use of 1,3,5-Triazinanes as Two-Atom Synthons3.2 Use of 1,3,5-Triazinanes as Three-Atom Synthons3.3 Use of 1,3,5-Triazinanes as Four-Atom Synthons3.4 Use of 1,3,5-Triazinanes as Six-Atom Synthons4 Conclusions

Recent Advances in the Tandem Cyclization/Cycloaddition of Allene Intermediates from Copper-Catalyzed Cross-Coupling of Diazo Compounds with Terminal Alkynes

Synthesis ◽  
2020 ◽  
Author(s):  
Shiyong Peng ◽  
Nuan Chen ◽  
Min He ◽  
Ting Zhou ◽  
Yuqi Zhu ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Short Review ◽  
Diazo Compounds ◽  
Terminal Alkynes ◽  
Recent Advances ◽  
Recent Developments ◽  
Tandem Cyclization ◽  
Cyclic Compounds

AbstractThis short review summarizes the most recent developments (since 2010) in the tandem cyclization/cycloaddition of allene intermediates­, generated from the copper-catalyzed cross-coupling of diazo compounds with terminal alkynes, to afford cyclic compounds.1 Introduction2 Cyclization2.1 Cyclization with Nucleophiles2.2 Cyclization with Electrophiles2.3 6π-Electrocyclization2.4 Other Cyclization3 Cycloaddition4 Conclusion

Recent Advances in Enantioselective C–C Bond Formation via Organocobalt Species

Synthesis ◽  
2018 ◽  
Vol 51 (01) ◽  
pp. 135-145 ◽  
Author(s):  
Naohiko Yoshikai
Keyword(s):  
Bond Formation ◽  
Cross Coupling ◽  
Short Review ◽  
Bond Forming ◽  
Carbon Nucleophiles ◽  
Recent Advances ◽  
Catalytic Intermediates ◽  
Bond Forming Reactions ◽  
Recent Developments

This Short Review describes recent developments in cobalt-catalyzed enantioselective C–C bond-forming reactions. The article focuses on reactions that most likely involve chiral organocobalt species as crucial catalytic intermediates and their mechanistic aspects.1 Introduction2 Hydrovinylation3 C–H Functionalization4 Cycloaddition and Cyclization5 Addition of Carbon Nucleophiles6 Cross-Coupling7 Conclusion

scholarly journals Decarboxylative sp3 C–N Coupling via Dual Copper/Photoredox Catalysis

2018 ◽  
Author(s):  
David W. C. MacMillan ◽  
Yufan Liang ◽  
Xiaheng Zhang
Keyword(s):  
Carboxylic Acids ◽  
Cross Coupling ◽  
Nickel Catalysis ◽  
Photoredox Catalysis ◽  
Drug Molecules ◽  
Rapid Construction ◽  
Coupling System ◽  
Tertiary Alkyl ◽  
Complex Drug

<p>Over the last three decades, significant progress has been made in the development of methods to construct <i>sp<sup>2</sup></i> C–N bonds using palladium, copper, or nickel catalysis. However, the incorporation of alkyl substrates to form <i>sp<sup>3</sup></i> C–N bonds remains one of the major challenges in the field of cross-coupling chemistry. Here, we demonstrate that the synergistic combination of copper catalysis and photoredox catalysis can provide a general platform to address this long-standing challenge. This novel cross-coupling system employs naturally abundant alkyl carboxylic acids and commercially available <i>N</i>-nucleophiles as coupling partners, and is applicable to a wide variety of primary, secondary, and tertiary alkyl carboxylic acids (via in situ iodonium activation). At the same time, a vast array of <i>N</i>-nucleophiles, including <i>N</i>-heterocycles, amides, sulfonamides, and anilines, can undergo C–N coupling to provide <i>N</i>-alkyl products in good to excellent efficiency at room temperature and in short order (5 minutes to 1 hour). We have also demonstrated that this C–N coupling protocol can be applied to substrates bearing multiple amines with high regioselectivity, as well as complex drug molecules, enabling the rapid construction of molecular complexity and the late stage functionalization of bioactive pharmaceuticals.</p>

Recent Advances in Csp3−Csp3 Cross-Coupling via Metallaphotoredox Strategy

Synthesis ◽  
2020 ◽  
Author(s):  
Weiming Yuan ◽  
Songlin Zheng ◽  
Yuanyuan Hu
Keyword(s):  
Organic Molecules ◽  
Cross Coupling ◽  
Short Review ◽  
Coupling Reactions ◽  
Organometallic Reagents ◽  
Cross Coupling Reactions ◽  
Recent Advances ◽  
Indispensable Tool ◽  
Metal Catalyzed ◽  
Important Progress

Transition metal-catalyzed carbon-carbon cross-coupling reactions have emerged the tremendous achievements in modern synthetic chemistry and to date explored as an indispensable tool for organic molecules construction. Despite important progress in this area, the theme of joining two C(sp3)-hybridized alkyl fragments remains yet elusive. So far, the existing methods have largely relied on using organometallic reagents as the nucleophilic coupling partners, thereby inevitably limiting functional groups compatibility. Although cross-electrophile coupling may alleviate the pain somewhat, it is necessary to add stoichiometric amounts of reductant to complete the catalytic cycle. Recently, the emergence of photoredox mediated single-electron transmetallation strategy evoked an ideal paradigm for selectively manipulating C(sp3)‒C(sp3) cross-coupling with unprecedented applying native C(sp3)-functionalities instead of organometallic reagents, thus opens a new window for C(sp3)‒C(sp3) bond creation. This short review will highlight the recent advances of the exciting subfield.

Nickel-catalyzed cross-coupling of O,N-chelated diarylborinates with aryl chlorides and mesylates

2019 ◽  
Vol 43 (3) ◽  
pp. 1589-1596 ◽  
Author(s):  
Chao Ren ◽  
Jingshu Zeng ◽  
Gang Zou
Keyword(s):  
Potassium Phosphate ◽  
Cross Coupling ◽  
Nickel Catalysis ◽  
Aryl Chlorides

Practical nickel catalysis for efficient cross-coupling of O,N-chelated diarylborinates with aryl chlorides and mesylates based on air-stable yet readily activated organonickel precursor, trans-NiCl(Ph)(PPh3)2, and sterically unsymmetrical N-heterocyclic carbene in situ generated from imidazolium precursor with trihydrate potassium phosphate in toluene.

scholarly journals Decarboxylative sp3 C–N Coupling via Dual Copper/Photoredox Catalysis

2018 ◽  
Author(s):  
David W. C. MacMillan ◽  
Yufan Liang ◽  
Xiaheng Zhang
Keyword(s):  
Carboxylic Acids ◽  
Cross Coupling ◽  
Nickel Catalysis ◽  
Photoredox Catalysis ◽  
Drug Molecules ◽  
Rapid Construction ◽  
Coupling System ◽  
Tertiary Alkyl ◽  
Complex Drug

<p>Over the last three decades, significant progress has been made in the development of methods to construct <i>sp<sup>2</sup></i> C–N bonds using palladium, copper, or nickel catalysis. However, the incorporation of alkyl substrates to form <i>sp<sup>3</sup></i> C–N bonds remains one of the major challenges in the field of cross-coupling chemistry. Here, we demonstrate that the synergistic combination of copper catalysis and photoredox catalysis can provide a general platform to address this long-standing challenge. This novel cross-coupling system employs naturally abundant alkyl carboxylic acids and commercially available <i>N</i>-nucleophiles as coupling partners, and is applicable to a wide variety of primary, secondary, and tertiary alkyl carboxylic acids (via in situ iodonium activation). At the same time, a vast array of <i>N</i>-nucleophiles, including <i>N</i>-heterocycles, amides, sulfonamides, and anilines, can undergo C–N coupling to provide <i>N</i>-alkyl products in good to excellent efficiency at room temperature and in short order (5 minutes to 1 hour). We have also demonstrated that this C–N coupling protocol can be applied to substrates bearing multiple amines with high regioselectivity, as well as complex drug molecules, enabling the rapid construction of molecular complexity and the late stage functionalization of bioactive pharmaceuticals.</p>

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