康 · 学术 | Reaction of the Day No. 1054
2023-08-11
临床研究
Remote C–H Olefination of
Heterocyclic Biaryls Enabled by Reversibly Bound
TemplatesLuo-Yan
Liu, Zhoulong Fan, Md Emdadul Hoque, Shaoqun Qian, Guangrong Meng, Nikita
Chekshin, Keita Tanaka,Jennifer
X. Qiao, Kap-Sun Yeung, and Jin-Quan YuDepartment of Chemistry, The Scripps
Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA)Discovery Chemistry, Bristol-Myers Squibb
Company, P.O. Box 4000, Princeton, New Jersey 08543, United StatesDiscovery
Chemistry, Bristol-Myers Squibb Research and Development, 100 BinneyStreet, Cambridge, MA 02142, United States—Angew. Chem. Int. Ed. 2023,
e202307581Recommended by Murong Xu_MC3ABSTRACT: Remote
C–H functionalization of heterocyclic biaryls will be of great importance in synthesis
and medicinal chemistry. Through adjusting the geometric relationship of the
directing atom and target C–H bonds, two new catalytic templates have been
developed to enable the functionalization of the more hindered ortho-C–H
bonds of heterobiaryls bearing directing heteroatom at the meta- or parapositions,
affording unprecedented site-selectivity. The use of template chaperone also
overcomes product inhibition and renders the directing templates catalytic. The
utility of this protocol was demonstrated by olefination of heterocyclic biaryls with
various substituents, overriding conventional steric and electronic effects.
These ortho-C–H olefinated heterobiaryls are
sterically hindered and can often be challenging to prepare through aryl-aryl
coupling reactions.Selected
substrate scope for ortho-C–H olefination of 3-phenylpyridinesSubstrate
scope for ortho-C–H
olefination of 4-phenylpyridinesSummary and CommentsProf.Jin-QuanYu al have
achieved site-selective remote C–H functionalization of 3- and
4-phenylpyridine biaryls,
with preferred reactivity at sterically disfavored ortho positions, another step towards broad molecular editing of various sites in
synthetic substrates. Although ortho-selectivity
is lower than 90% in some cases, this protocol offers an alternative and direct
approach to achieve these sterically demanding biaryl compounds, especially in the context of
late-stage functionalization. This reaction features broad substrate scope and
functional group compatibility.
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