Regioselective Synthesis and Slow-Release Suzuki鈥揗iyaura Cross-Coupling of MIDA Boronate-Functionalized Isoxazoles and Triazoles

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• 作者：Jonathan E. Grob ; Jill Nunez ; Michael A. Dechantsreiter ; Lawrence G. Hamann
• 刊名：Journal of Organic Chemistry
• 出版年：2011
• 出版时间：December 16, 2011
• 年：2011
• 卷：76
• 期：24
• 页码：10241-10248
• 全文大小：336K
• 年卷期：v.76,no.24(December 16, 2011)
• ISSN：1520-6904

文摘

The efficient preparation of heterocycles with a range of substitutions ortho to heteroatoms remains as a challenge in organic synthesis, particularly relevant to the construction of druglike molecules due to the ubiquitous presence of such moieties in that chemical space. Modular installation of heterocyclic building blocks using Suzuki鈥揗iyaura cross-coupling is a conceptually useful strategy to address this challenge, though this has historically been met with technical difficulty due to issues of inaccessibility and instability of the requisite heterocyclic boronates. Herein we report a mild and highly regioselective cycloaddition approach which affords convenient access to stable MIDA boronate-functionalized isoxazoles and triazoles and their subsequent efficient Suzuki鈥揗iyaura cross-coupling. This methodology is then further applied to a set of druglike compounds in an efficient one-pot telescoped sequence in line with green chemistry principles.