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A traceless organosilicon template-directed meta-selective-C-H alkenylation of phenols was realized with good yields and high selectivities. The template was readily removable through F-promoted O-Si cleavage under extremely mild conditions or recyclable through a p-TSA catalyzed process. The product was successfully applied in the preparation of a series of meta-alkenylated aromatic compounds.
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http://dx.doi.org/10.1039/c7cc07093d | DOI Listing |
Angew Chem Int Ed Engl
June 2024
Organisch-Chemisches Institut, Universität Münster, 48149, Münster, Germany.
C(sp)-H functionalization offers an efficient strategy for the synthesis of various elaborated N-containing heteroarenes. Along these lines, oxazino pyridines that can be readily prepared from pyridines, have been introduced as powerful substrates in radical- and ionic-mediated meta-C-H functionalization. However, the regioselective meta-C-H arylation of pyridines remains a great challenge.
View Article and Find Full Text PDFOrg Lett
July 2022
Department of Physics and Chemistry, DGIST, 333 Techno Jungang-daero, Dalseong-gun, Daegu 42988, Republic of Korea.
We describe -selective C-H functionalization of arylsilanes using a Si-tethered directing group. The current method enables a selective alkenylation of arenes bearing a variety of functional groups, and several electron-deficient olefins are also applicable as coupling partners. Further functional group transformations of the silicon-tethered directing group provide multisubstituted arenes efficiently.
View Article and Find Full Text PDFChem Sci
March 2020
Department of Chemistry, Imperial College London White City Campus, Molecular Sciences Research Hub 80 Wood Lane London W12 0BZ UK
-Methyliminodiacetic acid (MIDA) boronates are boronic acid derivatives which are stable to reduction, oxidation and transmetalation. This has led to their widespread use as boronic acid protecting groups (PGs) and in iterative cross-couplings. We describe herein the development of a novel MIDA derivative that acts in a dual manner, as a protecting group and a directing group (DG) for C(sp)-H functionalisation of arylboronic acids.
View Article and Find Full Text PDFOrg Lett
September 2018
School of Chemistry and Materials Science , Liaoning Shihua University, Fushun 113001 , China.
Rhodium(III)-catalyzed remote meta-selective-C-H alkenylation of phenol derivatives has been developed using a traceless organosilicon template as the directing group. This transformation proceeds smoothly with good yields and high meta-selectivities toward a series of phenol and alkene substrates. In addition, this protocol provides an effective strategy for late-stage transformations of various meta-alkenylated aromatic compounds.
View Article and Find Full Text PDFChem Commun (Camb)
December 2017
School of Chemistry and Materials Science, Liaoning Shihua University, Fushun 113001, China.
A traceless organosilicon template-directed meta-selective-C-H alkenylation of phenols was realized with good yields and high selectivities. The template was readily removable through F-promoted O-Si cleavage under extremely mild conditions or recyclable through a p-TSA catalyzed process. The product was successfully applied in the preparation of a series of meta-alkenylated aromatic compounds.
View Article and Find Full Text PDF