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A rhodium-catalyzed olefination of aliphatic aldehydes with arylboroxines is described. The simple rhodium­(I) complex [Rh­(cod)­OH]2 without any external ligands or additives is able to catalyze the reaction in air and neutral conditions, allowing the construction of aryl olefins in an efficient manner with a good functional group tolerance. The mechanistic investigation illustrates that the binary rhodium catalysis is the key for the transformation, which involves a Rh­(I)-catalyzed 1,2-addition and a Rh­(III)-catalyzed elimination.

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Transition-metal-catalyzed nucleophilic dearomatization of electron-deficient heteroarenes, such as pyridines, quinolines, isoquinolines and nitroindoles, has become a powerful method for the access of unsaturated heterocycles in recent decades. This short review summarizes nucleophilic dearomatization of electron-deficient heteroarenes with carbon- and heteroatom-based nucleophiles via transition-metal catalysis. A great number of functionalized heterocycles were obtained in this transformation. Importantly, many of these reactions were carried out in an enantioselective manner by means of asymmetric catalysis, providing a unique method for the construction of enantioenriched heterocycles. 1 Introduction 2 Transition-metal-catalyzed nucleophilic dearomatization of heteroarenes via alkynylation 3 Transition-metal-catalyzed nucleophilic dearomatization of heteroarenes via arylation 4 Transition-metal-catalyzed nucleophilic dearomatization of heteroarenes with other nucleophiles 5 Transition-metal-catalyzed nucleophilic dearomatization with nucleophiles formed in situ 6 Conclusion and outlook

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