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  • An efficient organocatalytic method for constructing biaryls through aromatic C-H activation.

An efficient organocatalytic method for constructing biaryls through aromatic C-H activation.

Nature chemistry (2010-11-26)
Chang-Liang Sun, Hu Li, Da-Gang Yu, Miao Yu, Xiao Zhou, Xing-Yu Lu, Kun Huang, Shu-Fang Zheng, Bi-Jie Li, Zhang-Jie Shi
ABSTRACT

The direct functionalization of C-H bonds has drawn the attention of chemists for almost a century. C-H activation has mainly been achieved through four metal-mediated pathways: oxidative addition, electrophilic substitution, σ-bond metathesis and metal-associated carbene/nitrene/oxo insertion. However, the identification of methods that do not require transition-metal catalysts is important because methods involving such catalysts are often expensive. Another advantage would be that the requirement to remove metallic impurities from products could be avoided, an important issue in the synthesis of pharmaceutical compounds. Here, we describe the identification of a cross-coupling between aryl iodides/bromides and the C-H bonds of arenes that is mediated solely by the presence of 1,10-phenanthroline as catalyst in the presence of KOt-Bu as a base. This apparently transition-metal-free process provides a new strategy with which to achieve direct C-H functionalization.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Potassium tert-butoxide, sublimed grade, 99.99% trace metals basis
Sigma-Aldrich
Potassium tert-butoxide, reagent grade, ≥98%
Sigma-Aldrich
Potassium tert-butoxide solution, 1.0 M in THF
Sigma-Aldrich
Potassium tert-butoxide ChemBeads