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Wikipedia Overview
Nucleophilic conjugate addition is a type of organic reaction. Ordinary nucleophilic additions or 1,2-nucleophilic additions deal mostly with additions to carbonyl compounds. Simple alkene compounds do not show 1,2 reactivity due to lack of polarity, unless the alkene is activated with special substituents. With α,β-unsaturated carbonyl compounds such as cyclohexenone it can be deduced from resonance structures that the β position is an electrophilic site which can react with a nucleophile. The negative charge in these structures is stored as an alkoxide anion. Such a nucleophilic addition is called a nucleophilic conjugate addition or 1,4-nucleophilic addition. The most important active alkenes are the aforementioned conjugated carbonyls and acrylonitriles.
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Copper-catalyzed enantioselective three-component radical 1,4-perfluoroalkylamination of 1,3-dienes - Nature
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Identifying Situations Where CTLA-4 Addition Improves NSCLC Outcomes - Targeted Oncology
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Enantioselective 1,4-Addition Reaction of α,β-Unsaturated Carboxylic Acids with Cycloalkanones Using Cooperative Chiral Amine–Boronic Acid Catalysts - Wiley Online Library
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Catalytic asymmetric reductive addition reactions using carbon electrophiles - ScienceDirect.com
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A cascade double 1,4-addition/intramolecular annulation strategy for expeditious assembly of unsymmetrical dibenzofurans - Nature
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Enantioselective Conjugate Addition of Aldehydes to Oxetane- and Azetidine-Containing Nitroolefins: An Entry to Spirocyclic Pyrrolidines - ACS Publications
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Rhodium(I)‐Catalyzed Asymmetric Cascade Reactions - Yang - 2025 - The Chemical Record - Wiley Online Library
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Umpolung reactivity of strained C–C σ-bonds without transition-metal catalysis - Nature
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Rules of Nucleophilic Additions to Zigzag Nanographene Diones** - Ribar - 2021 - Angewandte Chemie - Wiley Online Library
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Direct, Stereodivergent, and Catalytic Michael Additions of Thioimides to α,β-Unsaturated Aldehydes – Total Synthesis of Tapentadol - Wiley Online Library
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Transition from Kwon [4+2]- to [3+2]-cycloaddition enabled by AgF-assisted phosphine catalysis - Nature
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Dearomative di- and trifunctionalization of aryl sulfoxides via [5,5]-rearrangement - Nature
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Asymmetric Brønsted Acid Catalysis: Enantioselective Nucleophilic Substitutions and 1,4-Additions - Wiley Online Library
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The Enzymatic Asymmetric Conjugate Umpolung Reaction - Dresen - 2010 - Angewandte Chemie International Edition - Wiley Online Library
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The Long-Arm Effect: Influence of Axially Chiral Phosphoramidite Ligands on the Diastereo- and Enantioselectivity of the Tandem 1,4-Addition/Fluorination - Wiley Online Library
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Synthesis of novel fluorinated polymers: facile carbon–carbon bond formation aided by fluorine substituents - Nature
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Highly Selective Photomediated 1,4-Radical Addition to o -Quinones Controlled by a Self-Assembled Cage - Wiley Online Library
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Mimicry of Polyketide Synthases—Enantioselective 1,4-Addition Reactions of Malonic Acid Half-Thioesters to Nitroolefins - Wiley Online Library
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Chiral Copper(II)‐Catalyzed Enantioselective Boron Conjugate Additions to α,β‐Unsaturated Carbonyl Compounds in Water - Kobayashi - 2012 - Angewandte Chemie International Edition - Wiley Online Library
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Tandem 1,4-Addition/Enantioselective Protonation Catalyzed by Rhodium Complexes: Efficient Access to α-Amino Acids - Wiley Online Library
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