Pd-Catalyzed C–H Annulation of Five-Membered Heteroaryl Halides with Norbornene Derivatives

Pd-Catalyzed C–H Annulation of Five-Membered Heteroaryl Halides with Norbornene Derivatives

Complementary to Catellani-type reactions and 1:1 coupling of six-membered halo­(hetero)­arenes and norbornene (NBE) derivatives, Pd-catalyzed 1:2 coupling of five-membered haloheteroarenes with NBEs was achieved to afford rigid nonplanar heterocycles. Pyrazole, thiophene, furan, and indole underwen...

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Veröffentlicht in:ACS catalysis 2020-02, Vol.10 (3), p.1792-1798
Hauptverfasser: Padhi, Birakishore, Kang, Geunhee, Kim, Eunmin, Ha, Jeongmin, Kim, Hyun Tae, Lim, Jeewoo, Joo, Jung Min
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container_end_page 1798
container_issue 3
container_start_page 1792
container_title ACS catalysis
container_volume 10
creator Padhi, Birakishore
Kang, Geunhee
Kim, Eunmin
Ha, Jeongmin
Kim, Hyun Tae
Lim, Jeewoo
Joo, Jung Min
description Complementary to Catellani-type reactions and 1:1 coupling of six-membered halo­(hetero)­arenes and norbornene (NBE) derivatives, Pd-catalyzed 1:2 coupling of five-membered haloheteroarenes with NBEs was achieved to afford rigid nonplanar heterocycles. Pyrazole, thiophene, furan, and indole underwent exo- and trans-selective annulation. Two strained alkene groups of the resulting products were further manipulated to afford 1-alkylindazoles and ladder polymers. The type of heteroarenes and position of halides along with the choice of ligands and bases were critical to set a preference between C–H annulation and Catellani reactions, which will be useful for the development of Pd-catalyzed, NBE-mediated reactions of heteroarenes.
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title Pd-Catalyzed C–H Annulation of Five-Membered Heteroaryl Halides with Norbornene Derivatives
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