Practical and Modular Construction of C(sp3)-Rich Alkyl Boron Compounds
| Autor: | Jet Tsien, Jonathan M E Hughes, Ayala Ben David, Rohan R Merchant, Tian Qin, Yangyang Yang |
|---|---|
| Rok vydání: | 2020 |
| Předmět: |
inorganic chemicals
chemistry.chemical_classification Steric effects chemistry.chemical_element General Chemistry Modular construction 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry Catalysis 0104 chemical sciences chemistry.chemical_compound Colloid and Surface Chemistry chemistry Functional group Surface modification Boron Alkyl Material chemistry |
| Zdroj: | Journal of the American Chemical Society. 143:471-480 |
| ISSN: | 1520-5126 0002-7863 |
| Popis: | Alkyl boronic acids and esters play an important role in the synthesis of C(sp3)-rich medicines, agrochemicals, and material chemistry. This work describes a new type of transition-metal-free mediated transformation to enable the construction of C(sp3)-rich and sterically hindered alkyl boron reagents in a practical and modular manner. The broad generality and functional group tolerance of this method is extensively examined through a variety of substrates, including synthesis and late-stage functionalization of scaffolds relevant to medicinal chemistry. The strategic significance of this approach, with alkyl boronic acids as linchpins, is demonstrated through various downstream functionalizations of the alkyl boron compounds. This two-step concurrent cross-coupling approach, resembling formal and flexible alkyl-alkyl couplings, provides a general entry to synthetically challenging high Fsp3-containing drug-like scaffolds. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|