Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 6, Pages 2870-2877Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo3000805
Keywords
-
Categories
Funding
- Science Foundation Ireland
- Irish Research Council for Science, Engineering and Technology
- ERA-Chemistry
Ask authors/readers for more resources
The regioselective benzylic metalation of substituted toluenes using BuLi/KO-t-Bu/TMP(H) (LiNK metalation conditions) with subsequent in situ oxidative C-C coupling has been developed for the facile generation of 1,2-diarylethanes. A range of oxidants can be used for the oxidative coupling step, with 1,2-dibromoethane proving optimal. Heterocouplings can be achieved starting from a mixture of two different toluenes with a bias toward cross coupling achievable by using a 2-fold excess of one toluene starting material. The utility of this approach is illustrated by the synthesis of several biologically active natural products. A distinct advantage is that the synthetic steps typically required to preactivate the coupling substrates are eliminated and no transition metal is required to facilitate the C-C bond formation.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available