Sequential Processes in Palladium-Catalyzed Silicon-Based Cross-Coupling |
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Authors: | Scott E Denmark Jack Hung-Chang Liu |
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Affiliation: | Roger Adams Laboratory, University of Illinois at Urbana-Champaign, 600 South Mathews Avenue, Urbana, IL 61801, USA phone: +1 217 333-0066 fax: +1 217 333-3984 |
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Abstract: | Although developed somewhat later, silicon-based cross-coupling has become a viable alternative to the more conventional Suzuki–Miyaura, Stille–Kosugi–Migita, and Negishi cross-coupling reactions because of its broad substrate scope, high stability of silicon-containing reagents, and low toxicity of waste streams. An empowering and yet underappreciated feature unique to silicon-based cross-coupling is the wide range of sequential processes available. In these processes, simple precursors are first converted to complex silicon-containing cross-coupling substrates, and the subsequent silicon-based cross-coupling reaction affords an even more highly functionalized product in a stereoselective fashion. In so doing, structurally simple and inexpensive starting materials are quickly transformed into value-added and densely substituted products. Therefore, sequential processes are often useful in constructing the carbon backbones of natural products. In this review, studies of sequential processes involving silicon-based cross-coupling are discussed. Additionally, the total syntheses that utilize these sequential processes are also presented. |
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Keywords: | cross-coupling homogeneous catalysis palladium sequential processes silicon |
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