Regioselective C-H alkenylation of imidazoles and its application to the synthesis of unsymmetrically substituted benzimidazoles

Chemical Communications : Chem Comm
Hyeongwoo KimJung Min Joo

Abstract

A palladium-catalyzed C-H alkenylation of imidazoles has been developed. High C5 selectivity was achieved for C2-unsubstituted and C2-substituted imidazoles using oxygen and copper(ii) acetate, respectively, as oxidants. The obtained products were applied to benzannulation through a sequence involving transposition of N-alkyl groups to give C4-alkenyl imidazoles, alkenylation, thermal 6π-electrocyclization, and oxidation, affording unsymmetrically substituted benzimidazoles.

References

Apr 8, 2006·Science·Kamil Godula, Dalibor Sames
Feb 29, 2008·Organic Letters·Christian N KuzniewskiKarl-Heinz Altmann
Dec 24, 2008·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Wei ZhangJie Xu
Aug 10, 2010·Bioorganic & Medicinal Chemistry Letters·Yasushi TodorokiNobuhiro Hirai
Mar 12, 2011·Chemical Reviews·Jean Le Bras, Jacques Muzart
Aug 14, 2012·Angewandte Chemie·Junichiro YamaguchiKenichiro Itami
Nov 5, 2013·The Journal of Organic Chemistry·Emilie Van Den Berge, Raphaël Robiette
Jan 9, 2014·Chemical Communications : Chem Comm·Wei-Chih LeeTiow-Gan Ong
Sep 27, 2014·Angewandte Chemie·Yasutomo SegawaKenichiro Itami
May 20, 2015·Tetrahedron·Xiaolei Wang, Chuo Chen
Dec 17, 2015·Organic Letters·Shuai ChenAlessandro A Boezio
Dec 25, 2015·The Journal of Organic Chemistry·Su Jin HanJung Min Joo
Aug 19, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·Jia-Sheng OuyangFeng-Shou Liu
Jan 5, 2017·Chemical Reviews·Yoonsu ParkSukbok Chang
Jun 27, 2017·Journal of Medicinal Chemistry·Pietro PicconiKhondaker Miraz Rahman
Oct 5, 2017·Chemical Reviews·Dian WangShannon S Stahl

❮ Previous
Next ❯

Citations

Jan 7, 2020·Chemical Communications : Chem Comm·Fernando HerreraPedro Almendros
Apr 10, 2019·Organic & Biomolecular Chemistry·Andrey G LvovValerii Z Shirinian
Oct 5, 2018·Chemical & Pharmaceutical Bulletin·Takaya TogoMotomu Kanai
Oct 31, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Su ChenUpendra K Sharma
Aug 21, 2021·Organic Letters·Yaxi Dong, Bernhard Breit
Aug 14, 2019·The Journal of Organic Chemistry·Woohyeong LeeJung Min Joo
Dec 11, 2021·Accounts of Chemical Research·Siyeon Jeong, Jung Min Joo

❮ Previous
Next ❯

Related Concepts

Related Feeds

Anthelmintics

Anthelmintics or antihelminthics are a group of antiparasitic drugs that expel parasitic worms (helminths) and other internal parasites from the body by either stunning or killing them and without causing significant damage to the host. Discover the latest research on anthelmintics here.