Donor Rhodium Carbenes by Retro-Buchner Reaction
Mauro Mato
Institute of Chemical Research of Catalonia (ICIQ), Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007 Tarragona, Spain
Departament de Química Analítica i Química Orgànica, Universitat Rovira i Virgili, C/ Marcel⋅li Domingo s/n, 43007 Tarragona, Spain
Search for more papers by this authorCorresponding Author
Prof. Antonio M. Echavarren
Institute of Chemical Research of Catalonia (ICIQ), Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007 Tarragona, Spain
Departament de Química Analítica i Química Orgànica, Universitat Rovira i Virgili, C/ Marcel⋅li Domingo s/n, 43007 Tarragona, Spain
Search for more papers by this authorMauro Mato
Institute of Chemical Research of Catalonia (ICIQ), Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007 Tarragona, Spain
Departament de Química Analítica i Química Orgànica, Universitat Rovira i Virgili, C/ Marcel⋅li Domingo s/n, 43007 Tarragona, Spain
Search for more papers by this authorCorresponding Author
Prof. Antonio M. Echavarren
Institute of Chemical Research of Catalonia (ICIQ), Barcelona Institute of Science and Technology, Av. Països Catalans 16, 43007 Tarragona, Spain
Departament de Química Analítica i Química Orgànica, Universitat Rovira i Virgili, C/ Marcel⋅li Domingo s/n, 43007 Tarragona, Spain
Search for more papers by this authorGraphical Abstract
Successful iteration: Donor rhodium(II) carbenes are generated by retro-Buchner reaction (decarbenation) of 7-substituted 1,3,5-cycloheptatrienes, leading to broad-scope synthesis of allylsilanes by Si−H insertion and a new method for the iterative vinylogation of aldehydes.
Abstract
Rhodium carbenes are key intermediates in a range of cycloadditions and insertion reactions. Herein, we report the first generation of donor RhII carbenes by decarbenation of 7-substituted 1,3,5-cycloheptatrienes. This discovery unlocks an improved retro-Buchner-cyclopropanation sequence, a Si−H insertion reaction for a broad-scope synthesis of allylsilanes, and a new method for the vinylogation of aldehydes. The last strategy led to the development of an iterative synthesis of E-polyenes, and to the total synthesis of navenones B and C.
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