Transition-metal-catalyzed cross-coupling reactions have been well-established as indispensable tools in modern organic synthesis. One of the major research goals in cross-coupling area is expanding the scope of the coupling partners. In the past decade, diazo compounds (or their precursors N-tosylhydrazones) have emerged as nucleophilic cross-coupling partners in C–C single bond or C═C double bond formations in transition-metal-catalyzed reactions. This type of coupling reaction involves the following general steps. First, the organometallic species is generated by various processes, including oxidative addition, transmetalation, cyclization, C–C bond cleavage, and C–H bond activation. Subsequently, the organometallic species reacts with the diazo substrate to generate metal carbene intermediate, which undergoes rapid migratory insertion to form a C–C bond. The new organometallic species generated from migratory insertion may undergo various transformations. This type of carbene-based coupling has proven...

Transition-Metal-Catalyzed Cross-Couplings through Carbene Migratory Insertion

Hydrofunctionalisation and difunctionalisation of dienes, allenes, and alkynes are widely utilized in the synthesis of valuable allylic compounds. In the past decades, asymmetric catalysis has emerged as one of the most attractive fields in organic synthesis. Recently, the asymmetric versions of hydrofunctionalisation and difunctionalisation reactions have become powerful and compelling tools to afford enantiopure allylic compounds, appealing to a large range of chemists. Various metal complexes modified with a large number of chiral ligands and several chiral organocatalysts have been developed to promote the hydrofunctionalisation and difunctionalisation reactions and expand substrate scope. This review provides an overview of this field, and aims at summarizing the chiral ligand used in this area of research. A detailed discussion of the development of these reactions and the general reaction mechanisms is provided.

Asymmetric synthesis of allylic compounds via hydrofunctionalisation and difunctionalisation of dienes, allenes, and alkynes.

Three-component reactions can directly convert three reactants into the desired products in one pot and thus greatly shorten the synthetic path. Recently, transition-metal catalysis has been applied in the difunctionalization of alkenes and remarkable progress has been achieved to facilitate the construction of a wide range of functional molecules with high atom- and step-economic efficiency. This Focus Review highlights recent advances in this field.

Transition-Metal-Catalyzed Three-Component Difunctionalizations of Alkenes.

A method for the regiodivergent arylboration of dienes is presented. These reactions allow for the formation of a diverse range of synthetically versatile products from simple precursors. Through mechanistic studies, these reactions likely operate by initial addition of a Cu–Bpin complex across the diene followed by Pd-catalyzed cross coupling with an aryl halide or pseudohalide.

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Catalyst Controlled Regiodivergent Arylboration of Dienes

A photoinduced palladium-catalyzed 1,2-carbofunctionalization of conjugated dienes has been developed. This mild modular approach, which does not require employment of exogeneous photosensitizers a...

Photoinduced Palladium-Catalyzed Carbofunctionalization of Conjugated Dienes Proceeding via Radical-Polar Crossover Scenario: 1,2-Aminoalkylation and Beyond.

A novel highly enantioselective aminomethylamination of conjugated dienes with aminals catalyzed by a chiral palladium complex ligated with BINOL-derived chiral diphosphinite has been successfully developed. This reaction proceeds via a Pd-catalyzed cascade C-N bond activation, aminomethylation, and asymmetric allylic amination reaction under mild reaction conditions, providing a unique and efficient strategy for the synthesis of enantiomerically pure allylic 1,3-diamines.

Enantioselective Aminomethylamination of Conjugated Dienes with Aminals Enabled by Chiral Palladium Complex-Catalyzed C–N Bond Activation

Enantioselective Aminomethylamination of Conjugated Dienes with Aminals Enabled by Chiral Palladium Complex-Catalyzed C-N Bond Activation.

Palladium-catalysed cross-coupling of aminals with N-sulfonyl hydrazones has been established via C–N bond activation under base-free conditions, in which one C–C bond and one C–S bond were simultaneously generated. It was successfully applied in the construction of a variety of aminomethyl substituted allylic sulfones. Preliminary mechanistic studies indicated that the unique electrophilic cyclopalladated complex was involved in the catalytic cycle.

Palladium-catalysed coupling reaction of aminals with N-sulfonyl hydrazones to give allylic sulfones

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Enantioselective Aminomethylamination of Conjugated Dienes with Aminals Enabled by Chiral Palladium Complex-Catalyzed C–N Bond Activation

Enantioselective Aminomethylamination of Conjugated Dienes with Aminals Enabled by Chiral Palladium Complex-Catalyzed C-N Bond Activation.

Palladium-catalysed coupling reaction of aminals with N-sulfonyl hydrazones to give allylic sulfones