Diverse functionalization of strong alkyl C–H bonds by undirected borylation

doi:10.1126/science.aba6146

GSTDTAP > 气候变化

DOI	10.1126/science.aba6146
	Diverse functionalization of strong alkyl C–H bonds by undirected borylation
	Raphael Oeschger; Bo Su; Isaac Yu; Christian Ehinger; Erik Romero; Sam He; John Hartwig
	2020-05-15
发表期刊	Science
出版年	2020
英文摘要	Catalytic borylation is the rare reaction that can selectively target stronger over weaker saturated carbon–hydrogen (C–H) bonds. However, the trade-off has been that the reaction is slow and requires high excess of the hydrocarbon. Oeschger et al. now report that the right ligand (2-methylphenanthroline) coordinated to iridium can accelerate the reaction by 50- to 80-fold. This rate enhancement enables selective borylation of primary C–H bonds with the hydrocarbon as limiting reagent. The reaction is also unusually selective for β-C–H bonds in saturated heterocycles. Science , this issue p. [736][1] The selective functionalization of strong, typically inert carbon-hydrogen (C–H) bonds in organic molecules is changing synthetic chemistry. However, the undirected functionalization of primary C–H bonds without competing functionalization of secondary C–H bonds is rare. The borylation of alkyl C–H bonds has occurred previously with this selectivity, but slow rates required the substrate to be the solvent or in large excess. We report an iridium catalyst ligated by 2-methylphenanthroline with activity that enables, with the substrate as limiting reagent, undirected borylation of primary C–H bonds and, when primary C–H bonds are absent or blocked, borylation of strong secondary C–H bonds. Reactions at the resulting carbon-boron bond show how these borylations can lead to the installation of a wide range of carbon-carbon and carbon-heteroatom bonds at previously inaccessible positions of organic molecules. [1]: /lookup/doi/10.1126/science.aba6146
领域	气候变化 ; 资源环境
URL	查看原文
引用统计
文献类型	期刊论文
条目标识符	http://119.78.100.173/C666/handle/2XK7JSWQ/267714
专题	气候变化资源环境科学
推荐引用方式 GB/T 7714	Raphael Oeschger,Bo Su,Isaac Yu,等. Diverse functionalization of strong alkyl C–H bonds by undirected borylation[J]. Science,2020.
APA	Raphael Oeschger.,Bo Su.,Isaac Yu.,Christian Ehinger.,Erik Romero.,...&John Hartwig.(2020).Diverse functionalization of strong alkyl C–H bonds by undirected borylation.Science.
MLA	Raphael Oeschger,et al."Diverse functionalization of strong alkyl C–H bonds by undirected borylation".Science (2020).