Rhodium(III)-Catalyzed C(sp2)–H Chemoselective Annulation to O‑Cyclized Isochromen-imines from Benzamides

Through the development of ligands and reaction conditions, the Rh­(III)-catalyzed selective annulation of benzamides with internal alkynes has been achieved to the formation of O-cyclized isochromen-imines. Various substituents are well-tolerated under mild reaction conditions. Density functional t...

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Published in:Organic letters 2020-12, Vol.22 (24), p.9462-9467
Main Authors: Zhang, Ping, Chang, Wenju, Kang, Yan-Shang, Zhao, Wenxuan, Cui, Pei-Pei, Liang, Yong, Sun, Wei-Yin, Lu, Yi
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cited_by cdi_FETCH-LOGICAL-a411t-1482be2667d1a009e1792fd529c73aad8bebe67f2884fe1a03bebccd5cee34113
cites cdi_FETCH-LOGICAL-a411t-1482be2667d1a009e1792fd529c73aad8bebe67f2884fe1a03bebccd5cee34113
container_end_page 9467
container_issue 24
container_start_page 9462
container_title Organic letters
container_volume 22
creator Zhang, Ping
Chang, Wenju
Kang, Yan-Shang
Zhao, Wenxuan
Cui, Pei-Pei
Liang, Yong
Sun, Wei-Yin
Lu, Yi
description Through the development of ligands and reaction conditions, the Rh­(III)-catalyzed selective annulation of benzamides with internal alkynes has been achieved to the formation of O-cyclized isochromen-imines. Various substituents are well-tolerated under mild reaction conditions. Density functional theory calculations indicate that silver carbonate could act as a Lewis acid to assist the ligand to improve the chemical selectivity of the reaction in a catalytic system.
doi_str_mv 10.1021/acs.orglett.0c03425
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title Rhodium(III)-Catalyzed C(sp2)–H Chemoselective Annulation to O‑Cyclized Isochromen-imines from Benzamides
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