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 inOrganic letters Vol. 22; no. 24; pp. 9462 - 9467
Main Authors Zhang, Ping, Chang, Wenju, Kang, Yan-Shang, Zhao, Wenxuan, Cui, Pei-Pei, Liang, Yong, Sun, Wei-Yin, Lu, Yi
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.12.2020
Amer Chemical Soc
Subjects
alkynes
benzamides
carbonates
Chemistry
Chemistry, Organic
chemoselectivity
density functional theory
Lewis acids
ligands
Physical Sciences
rhodium
Science & Technology
silver
FUNCTIONALIZATION
AROMATIC AMIDES
MECHANISTIC INSIGHTS
CATALYZED SYNTHESIS
RH
BOND FORMATION
OXIDATIVE ANNULATION
ALKYNES
C-H ACTIVATION
DIRECT DEHYDROGENATIVE ANNULATION
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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.
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content type line 23
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.0c03425