Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 143, Issue 1, Pages 471-480Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c11964
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Funding
- Robert A. Welch Foundation [I-2010-20190330]
- Eugene McDermott Scholar Endowed Scholarship
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This research introduces a new transition-metal-free mediated transformation for the construction of C(sp(3))-rich and sterically hindered alkyl boron reagents. The method shows broad generality and functional group tolerance, making it suitable for the synthesis and functionalization of medicinal chemistry scaffolds. The strategic significance of using alkyl boronic acids as linchpins is demonstrated through downstream functionalizations of the alkyl boron compounds.
Alkyl boronic acids and esters play an important role in the synthesis of C(sp(3))-rich medicines, agrochemicals, and material chemistry. This work describes a new type of transition-metal-free mediated transformation to enable the construction of C(sp(3))-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 Fsp(3)-containing drug-like scaffolds.
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