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Directing group-free approaches for three-component catalytic dicarbofunctionalization of unactivated alkenes

Hongyu Wang, Ming Joo Koh

2022Cell Reports Physical Science26 citationsDOIOpen Access PDF

Abstract

The generation of value-added compounds from abundant feedstock chemicals through operationally simple methods is a long-standing objective in organic synthesis. Regioselective three-component 1,2-dicarbofunctionalization of unactivated alkenes has emerged as a powerful strategy for introducing molecular complexity via two sequential C−C bond formations. However, inherent challenges, such as undesired β-hydride elimination and the poor reactivity of unbiased C=C bonds, hindered the development of this field. Although these problems may be partially addressed with directing auxiliaries incorporated within the alkene substrate, the additional procedures required for installing and removing these auxiliaries limited their overall utility in chemistry. In light of this deliberation, the directing group-free approach represents a complementary and promising approach for implementing 1,2-dicarbofunctionalization. In this perspective, we summarize the related catalytic regimes with their associated mechanisms, highlighting the differences in the scope of products obtained. Finally, we present the remaining challenges and opportunities for future breakthroughs in the field.

Topics & Concepts

AlkeneRegioselectivityScope (computer science)Reactivity (psychology)Biochemical engineeringComponent (thermodynamics)Substrate (aquarium)Combinatorial chemistryChemistryCatalysisOrganic chemistryComputer scienceEngineeringThermodynamicsPhysicsPathologyProgramming languageGeologyMedicineOceanographyAlternative medicineCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsCyclopropane Reaction Mechanisms
Directing group-free approaches for three-component catalytic dicarbofunctionalization of unactivated alkenes | Litcius