Recent Advances in C(sp3)–C(sp3) Cross-Coupling Chemistry: A Dominant Performance of Nickel Catalysts

Nickel and Palladium Catalysis: Stronger Demand than Ever

(2022) Victor M. Chernyshev et al.   ACS Catalysis

Metallaphotoredox: The Merger of Photoredox and Transition Metal Catalysis

(2021) Amy Y. Chan et al.   CHEMICAL REVIEWS

Nickel-Catalyzed Alkyl–Alkyl Cross-Electrophile Coupling Reaction of 1,3-Dimesylates for the Synthesis of Alkylcyclopropanes

(2020) Amberly B. Sanford et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Catalyst-controlled doubly enantioconvergent coupling of racemic alkyl nucleophiles and electrophiles

(2020) Haohua Huo et al.   SCIENCE

Mechanisms of Nickel-Catalyzed Coupling Reactions and Applications in Alkene Functionalization

(2020) Justin Diccianni et al.   ACCOUNTS OF CHEMICAL RESEARCH

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

(2020) Weiming Yuan et al.   SYNTHESIS-STUTTGART

Enantioconvergent Cross−Couplings of Alkyl Electrophiles: The Catalytic Asymmetric Synthesis of Organosilanes

(2019) Gregory C Fu   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Enantioselective Construction of alpha-Chiral Silanes by Nickel-Catalyzed C(sp3)-C(sp3) Cross-Coupling

(2019) Hong Yi et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Mechanistic Characterization of (Xantphos)Ni(I)-Mediated Alkyl Bromide Activation: Oxidative Addition, Electron Transfer, or Halogen-Atom Abstraction

(2019) Justin B. Diccianni et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Harnessing Alkylpyridinium Salts as Electrophiles in Deaminative Alkyl–Alkyl Cross-Couplings

(2019) Shane Plunkett et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Tetrahydrothiopyran-4-one as Five-Carbon Source for Scalable Synthesis of (±)-Tapentadol

(2019) Ramagonolla Kranthikumar et al.   ORGANIC PROCESS RESEARCH & DEVELOPMENT

Ni-catalyzed deaminative cross-electrophile coupling of Katritzky salts with halides via C─N bond activation

(2019) Shengyang Ni et al.   Science Advances

Nickel/Cobalt-Catalyzed C(sp3)–C(sp3) Cross-Coupling of Alkyl Halides with Alkyl Tosylates

(2019) Kimihiro Komeyama et al.   ACS Catalysis

Mn-Enabled Radical-Based Alkyl–Alkyl Cross-Coupling Reaction from 4-Alkyl-1,4-dihydropyridines

(2019) Jie Wang et al.   JOURNAL OF ORGANIC CHEMISTRY

Pd Metal Catalysts for Cross-Couplings and Related Reactions in the 21st Century: A Critical Review

(2018) Andrea Biffis et al.   CHEMICAL REVIEWS

Iron-catalyzed Alkyl–Alkyl Negishi Coupling of Organoaluminum Reagents

(2018) Ryosuke Agata et al.   CHEMISTRY LETTERS

Metallaphotoredox-Catalyzed Cross-Electrophile Csp3–Csp3 Coupling of Aliphatic Bromides

(2018) Russell T. Smith et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Selective sp3 C–H alkylation via polarity-match-based cross-coupling

(2017) Chip Le et al.   NATURE

Transition metal–catalyzed alkyl-alkyl bond formation: Another dimension in cross-coupling chemistry

(2017) Junwon Choi et al.   SCIENCE

Insertion of N-Tosylacetimidates/Acetimidamides onto Arynes via [2 + 2] Cycloaddition

(2016) Ramagonolla Kranthikumar et al.   JOURNAL OF ORGANIC CHEMISTRY

Metallaphotoredox-catalysed sp3–sp3 cross-coupling of carboxylic acids with alkyl halides

(2016) Craig P. Johnston et al.   NATURE

The Ireland–Claisen rearrangement strategy towards the synthesis of the schizophrenia drug, (+)-asenapine

(2016) Raghunath Reddy Anugu et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

A general, modular method for the catalytic asymmetric synthesis of alkylboronate esters

(2016) J. Schmidt et al.   SCIENCE

A general alkyl-alkyl cross-coupling enabled by redox-active esters and alkylzinc reagents

(2016) T. Qin et al.   SCIENCE

1,4-Dihydropyridines as Alkyl Radical Precursors: Introducing the Aldehyde Feedstock to Nickel/Photoredox Dual Catalysis

(2016) Álvaro Gutiérrez-Bonet et al.   ACS Catalysis

Active Species and Mechanistic Pathways in Iron-Catalyzed C–C Bond-Forming Cross-Coupling Reactions

(2016) Carlo Cassani et al.   ACS Catalysis

Nickel-Catalyzed Alkyl-Alkyl Cross-Couplings of Fluorinated Secondary Electrophiles: A General Approach to the Synthesis of Compounds having a Perfluoroalkyl Substituent

(2015) Yufan Liang et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C–C Bonds

(2015) Alan H. Cherney et al.   CHEMICAL REVIEWS

Palladium-Catalyzed Regioselective Domino Cyclization of Cyclohexadienones

(2015) Akondi Srirama Murthy et al.   JOURNAL OF ORGANIC CHEMISTRY

Stereospecific Intramolecular Reductive Cross-Electrophile Coupling Reactions for Cyclopropane Synthesis

(2015) Emily J. Tollefson et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Tutorial on Oxidative Addition

(2015) Jay A. Labinger   ORGANOMETALLICS

Nickel-catalyzed reductive coupling of alkyl halides with other electrophiles: concept and mechanistic considerations

(2015) Jun Gu et al.   Organic Chemistry Frontiers

Stereospecific Nickel-Catalyzed Cross-Coupling Reactions of Alkyl Grignard Reagents and Identification of Selective Anti-Breast-Cancer Agents

(2014) Ivelina M. Yonova et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Copper-Catalyzed Reductive Cross-Coupling of Nonactivated Alkyl Tosylates and Mesylates with Alkyl and Aryl Bromides

(2014) Jing-Hui Liu et al.   CHEMISTRY-A EUROPEAN JOURNAL

Copper-Catalyzed Alkyl–Alkyl Cross-Coupling Reactions Using Hydrocarbon Additives: Efficiency of Catalyst and Roles of Additives

(2014) Takanori Iwasaki et al.   JOURNAL OF ORGANIC CHEMISTRY

Cross-Electrophile Coupling: Principles of Reactivity and Selectivity

(2014) Daniel A. Everson et al.   JOURNAL OF ORGANIC CHEMISTRY

sp3-sp3 Coupling reactions in the synthesis of natural products and biologically active molecules

(2014) Egor Geist et al.   NATURAL PRODUCT REPORTS

Recent advances in homogeneous nickel catalysis

(2014) Sarah Z. Tasker et al.   NATURE

Nickel-Catalyzed Reductive Methylation of Alkyl Halides and Acid Chlorides with Methyl p-Tosylate

(2014) Zhuye Liang et al.   ORGANIC LETTERS

Merging photoredox with nickel catalysis: Coupling of  -carboxyl sp3-carbons with aryl halides

(2014) Z. Zuo et al.   SCIENCE

Enantioconvergent Cross-Couplings of Racemic Alkylmetal Reagents with Unactivated Secondary Alkyl Electrophiles: Catalytic Asymmetric Negishi α-Alkylations of N-Boc-pyrrolidine

(2013) Christopher J. Cordier et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Combined Experimental and Theoretical Study on the Reductive Cleavage of Inert C–O Bonds with Silanes: Ruling out a Classical Ni(0)/Ni(II) Catalytic Couple and Evidence for Ni(I) Intermediates

(2013) Josep Cornella et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Functional-Group-Tolerant, Nickel-Catalyzed Cross-Coupling Reaction for Enantioselective Construction of Tertiary Methyl-Bearing Stereocenters

(2013) Hanna M. Wisniewska et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

A Structurally Rigid Bis(amido) Ligand Framework in Low-Coordinate Ni(I), Ni(II), and Ni(III) Analogues Provides Access to a Ni(III) Methyl Complex via Oxidative Addition

(2013) Michael I. Lipschutz et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Nickel-Catalyzed Carbon–Carbon Bond-Forming Reactions of Unactivated Tertiary Alkyl Halides: Suzuki Arylations

(2013) Susan L. Zultanski et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Palladium-Catalyzed Picolinamide-Directed Alkylation of Unactivated C(sp3)–H Bonds with Alkyl Iodides

(2013) Shu-Yu Zhang et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Nickel-catalyzed cross-coupling of unactivated alkyl halides using bis(pinacolato)diboron as reductant

(2013) Hailiang Xu et al.   Chemical Science

Palladium-Catalyzed Cross-Coupling: A Historical Contextual Perspective to the 2010 Nobel Prize

(2012) Carin C. C. Johansson Seechurn et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Copper-catalyzed coupling reaction of unactivated secondary alkyl iodides with alkyl Grignard reagents in the presence of 1,3-butadiene as an effective additive

(2012) Ruwei Shen et al.   CHEMICAL COMMUNICATIONS

Methyl Effects on Protein–Ligand Binding

(2012) Cheryl S. Leung et al.   JOURNAL OF MEDICINAL CHEMISTRY

Catalytic Enantioselective Cross-Couplings of Secondary Alkyl Electrophiles with Secondary Alkylmetal Nucleophiles: Negishi Reactions of Racemic Benzylic Bromides with Achiral Alkylzinc Reagents

(2012) Jörg T. Binder et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

New Directing Groups for Metal-Catalyzed Asymmetric Carbon–Carbon Bond-Forming Processes: Stereoconvergent Alkyl–Alkyl Suzuki Cross-Couplings of Unactivated Electrophiles

(2012) Ashraf Wilsily et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Nickel-Catalyzed Coupling Reactions of Alkyl Electrophiles, Including Unactivated Tertiary Halides, To Generate Carbon–Boron Bonds

(2012) Alexander S. Dudnik et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Traceless Directing Group for Stereospecific Nickel-Catalyzed Alkyl−Alkyl Cross-Coupling Reactions

(2012) Margaret A. Greene et al.   ORGANIC LETTERS

Nickel-Catalyzed Diastereoselective Alkyl–Alkyl Kumada Coupling Reactions

(2012) Pablo M. Perez Garcia et al.   ORGANIC LETTERS

Fe-catalysed Kumada-type alkyl–alkyl cross-coupling. Evidence for the intermediacy of Fe(i) complexes

(2012) Manuel Guisán-Ceinos et al.   Chemical Science

Escape from Flatland 2: complexity and promiscuity

(2012) Frank Lovering   MedChemComm

The Methylation Effect in Medicinal Chemistry

(2011) Eliezer J. Barreiro et al.   CHEMICAL REVIEWS

Advances in Transition Metal (Pd,Ni,Fe)-Catalyzed Cross-Coupling Reactions Using Alkyl-organometallics as Reaction Partners

(2011) Ranjan Jana et al.   CHEMICAL REVIEWS

Decarboxylative coupling reactions: a modern strategy for C–C-bond formation

(2011) Nuria Rodríguez et al.   CHEMICAL SOCIETY REVIEWS

A Structure–Activity Study of Ni-Catalyzed Alkyl–Alkyl Kumada Coupling. Improved Catalysts for Coupling of Secondary Alkyl Halides

(2011) Peng Ren et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Catalytic Asymmetric γ-Alkylation of Carbonyl Compounds via Stereoconvergent Suzuki Cross-Couplings

(2011) Susan L. Zultanski et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Stereoconvergent Amine-Directed Alkyl–Alkyl Suzuki Reactions of Unactivated Secondary Alkyl Chlorides

(2011) Zhe Lu et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Nickel-Catalyzed Reductive Cross-Coupling of Unactivated Alkyl Halides

(2011) Xiaolong Yu et al.   ORGANIC LETTERS

Nickel-catalyzed cross coupling of non-activated alkyl halides: a mechanistic perspective

(2011) Xile Hu   Chemical Science

Alkyl-Alkyl Suzuki Cross-Coupling of Unactivated Secondary Alkyl Chlorides

(2010) Zhe Lu et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Nickel-catalyzed, sodium iodide-promoted reductive dimerization of alkyl halides, alkyl pseudohalides, and allylic acetates

(2010) Michael R. Prinsell et al.   CHEMICAL COMMUNICATIONS

Asymmetric Alkyl−Alkyl Cross-Couplings of Unactivated Secondary Alkyl Electrophiles: Stereoconvergent Suzuki Reactions of Racemic Acylated Halohydrins

(2010) Nathan A. Owston et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Nickel-Catalyzed Cross-Coupling of Non-activated and Functionalized Alkyl Halides with Alkyl Grignard Reagents

(2009) Oleg Vechorkin et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Nickel-catalysed Negishi cross-coupling reactions: scope and mechanisms

(2009) Vilas B. Phapale et al.   CHEMICAL SOCIETY REVIEWS

Escape from Flatland: Increasing Saturation as an Approach to Improving Clinical Success

(2009) Frank Lovering et al.   JOURNAL OF MEDICINAL CHEMISTRY

Sn-Free Ni-Catalyzed Reductive Coupling of Glycosyl Bromides with Activated Alkenes

(2009) Hegui Gong et al.   ORGANIC LETTERS

Nickel-Catalyzed Negishi Cross-Couplings of Secondary Nucleophiles with Secondary Propargylic Electrophiles at Room Temperature

(2008) Sean W. Smith et al.   ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

Nickel-Catalyzed Asymmetric Negishi Cross-Couplings of Secondary Allylic Chlorides with Alkylzincs

(2008) Sunghee Son et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Enantioselective Alkyl−Alkyl Suzuki Cross-Couplings of Unactivated Homobenzylic Halides

(2008) Bunnai Saito et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Nickel Complexes of a Pincer NN2Ligand: Multiple Carbon−Chloride Activation of CH2Cl2and CHCl3Leads to Selective Carbon−Carbon Bond Formation

(2008) Zsolt Csok et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY