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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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Bibliographic Details
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
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c03425