4.2.8. Reductive Coupling 3109 5. Reaction of Aromatic Compounds 3110 5.1. Electrophilic Substitutions 3110 5.2. Radical Substitution 3111 5.3. Oxidative Coupling 3111 5.4. Photochemical Reactions 3111 6. Reaction of Carbonyl Compounds 3111 6.1. Nucleophilic Additions 3111 6.1.1. Allylation 3111 6.1.2. Propargylation 3120 6.1.3. Benzylation 3121 6.1.4. Arylation/Vinylation 3121 6.1.5. Alkynylation 3121 6.1.6. Alkylation 3121 6.1.7. Reformatsky-Type Reaction 3122 6.1.8. Direct Aldol Reaction 3122 6.1.9. Mukaiyama Aldol Reaction 3124 6.1.10. Hydrogen Cyanide Addition 3125 6.2. Pinacol Coupling 3126 6.3. Wittig Reactions 3126 7. Reaction of R,â-Unsaturated Carbonyl Compounds 3127

Organic Reactions in Aqueous Media with a Focus on Carbon−Carbon Bond Formations: A Decade Update

Green chemistry for chemical synthesis addresses our future challenges in working with chemical processes and products by inventing novel reactions that can maximize the desired products and minimize by-products, designing new synthetic schemes and apparati that can simplify operations in chemical productions, and seeking greener solvents that are inherently environmentally and ecologically benign

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Green chemistry for chemical synthesis

Organic syntheses using indium-mediated and catalyzed reactions in aqueous media

Aqueous Barbier-Grignard type reaction: Scope, mechanism, and synthetic applications

Despite the enormous research efforts in recent years regarding lignin depolymerisation and functionalisation, few commercial products are available. This review provides a summary and viewpoint of extensive research in the lignin-to-product valorisation chain, with an emphasis on downstream processing of lignin derived feedstock into end products. It starts with an introduction of available platform chemicals and polymeric derivatives generated from lignin via existing depolymerisation and functionalisation technologies. Following that, detailed analyses of various strategies for the downstream processing of lignin derived platform chemicals and materials into fuels, valued-added chemicals and functional polymers are provided. A concise techno-economic analysis of various downstream processes is conducted based on the market demand of the end product, economic potential and technological readiness, enabling the identification of processes that are potentially both economically competitive and commercially feasible, and shedding light on processes which deserve further technological development. We wish this review will stimulate further advances in the sustainable production of value-added products from lignin to integrate this invaluable “bio-waste” into the chemical/materials supply chain.

Downstream processing of lignin derived feedstock into end products.

Organometallic reactions in aqueous media with indium

The sialic acid KDN is synthesized stereoselectively in three steps from D-mannose by taking advantage of an indium mediated coupling reaction in aqueous medium.

A concise chemical synthesis of (+)-3-deoxy-D-glycero-D-galacto-nonulosonic acid (KDN)

Various difunctionalizations of acrylamide can not only provide a simple approach to form a wide scope of functionalized oxindoles, but can also be applied and generated easily. This review concludes different difunctionalizations of acrylamide to synthesize oxindoles based on the mechanistic aspects. The goal is to encourage further mechanistic studies hopefully leading to an in-depth understanding of this strategy.

Various difunctionalizations of acrylamide: an efficient approach to synthesize oxindoles

Palladium-catalyzed allylic alkylation of nonstabilized carbon nucleophiles is difficult and remains a major challenge. Reported here is a highly chemo- and regioselective direct palladium-catalyzed C-allylation of hydrazones, generated from carbonyls, as a source of umpolung unstabilized alkyl carbanions and surrogates of alkyl organometallic reagents. Contrary to classical allylation techniques, this umpolung reaction utilizes hydrazones prepared not only from aryl aldehydes but also from alkyl aldehydes and ketones as renewable feedstocks. This strategy complements the palladium-catalyzed coupling of unstabilized nucleophiles with allylic electrophiles by providing an efficient and selective catalytic alternative to the traditional use of highly reactive alkyl organometallic reagents.

Umpolung of Carbonyl Groups as Alkyl Organometallic Reagent Surrogates for Palladium-Catalyzed Allylic Alkylation.

Primary anilines are essential building blocks to synthesize various pharmaceuticals, agrochemicals, pigments, electronic materials, and others. To date, the syntheses of primary anilines mostly rely on the reduction of nitroarenes or the transition-metal-catalyzed Ullmann, Buchwald–Hartwig and Chan–Lam cross-coupling reactions with ammonia, in which non-renewable petroleum-based chemicals are typically used as feedstocks via multiple step syntheses. A long-standing scientific challenge is to synthesize various primary anilines directly from renewable sources. Herein, we report a general method to directly convert a broad range of phenols into the corresponding primary anilines with the cheap and widely available hydrazine as both amine and hydride sources with simple Pd/C as the catalyst.

/pdf/direct-conversion-of-phenols-into-primary-anilines-with-18o9mdq2h8.pdf

Chen-Chen Li

Papers

Organometallic reactions in aqueous media with indium

A concise chemical synthesis of (+)-3-deoxy-D-glycero-D-galacto-nonulosonic acid (KDN)

Various difunctionalizations of acrylamide: an efficient approach to synthesize oxindoles

Umpolung of Carbonyl Groups as Alkyl Organometallic Reagent Surrogates for Palladium-Catalyzed Allylic Alkylation.

Direct conversion of phenols into primary anilines with hydrazine catalyzed by palladium