title: Sequential Processes in Palladium-Catalyzed Silicon-Based Cross-Coupling.
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.
authors.affiliation: Roger Adams Laboratory University of Illinois at Urbana-Champaign 600 South Mathews Avenue Urbana, IL 61801 (USA).
authors.forename: Scott E
authors.initials: SE
authors.lastname: Denmark
authors.forename: Jack H-C
authors.initials: JH
authors.lastname: Liu