From Esters to Benzodiazepines: A Two-Step Nickel–Iridium Catalytic Pathway via Amide Intermediates

Abstract Herein, we report a NiCl2·DPEPhos catalyzed chemoselective activation of the C(acyl)–O bond in functionalized esters toward the synthesis of amino-hydroxy-amides using ambident amino alcohols. [IrCp*Cl2]2 catalyzed intramolecular cyclization of amino-hydroxy-amides via borrowing hydrogenation, afforded therapeutically beneficial 1,4-benzodiazepin-5-ones. A plausible mechanism for both steps has been elucidated. The 1,4-benzodiazepin-5-one frameworks were structurally diversified through postsynthetic modification. This protocol enables access to natural products such as Circumdatin F and Circumdatin H, further underscoring its potential.

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Publication Details

Journal
Organic Letters
Published
2026-08-20
DOI
https://doi.org/10.1021/acs.orglett.6c02844
Primary Topic
Asymmetric Hydrogenation and Catalysis
Type
article
Field-Weighted Citation Impact
0.00

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article

From Esters to Benzodiazepines: A Two-Step Nickel–Iridium Catalytic Pathway via Amide Intermediates

P. Madhavan Nair, Boopathy Gnanaprakasam, Himani Priya, Manikandan Paranjothy et al.
Organic Letters
Asymmetric Hydrogenation and Catalysis
article

From Esters to Benzodiazepines: A Two-Step Nickel–Iridium Catalytic Pathway via Amide Intermediates

P. Madhavan Nair, Boopathy Gnanaprakasam, Himani Priya, Manikandan Paranjothy, Gourishankar B. Swami, Bhakti M. Bate, Abhijit V. More
article en

Abstract

Abstract Herein, we report a NiCl2·DPEPhos catalyzed chemoselective activation of the C(acyl)–O bond in functionalized esters toward the synthesis of amino-hydroxy-amides using ambident amino alcohols. [IrCp*Cl2]2 catalyzed intramolecular cyclization of amino-hydroxy-amides via borrowing hydrogenation, afforded therapeutically beneficial 1,4-benzodiazepin-5-ones. A plausible mechanism for both steps has been elucidated. The 1,4-benzodiazepin-5-one frameworks were structurally diversified through postsynthetic modification. This protocol enables access to natural products such as Circumdatin F and Circumdatin H, further underscoring its potential.

Organic Letters
Indian Institute of Science Education and Research Kolkata (IN), Indian Institute of Science Education and Research Pune (IN), Indian Institute of Technology Indore (IN)
Council of Scientific and Industrial Research, India, University Grants Commission, Indian Institute of Science Education and Research Pune, Science and Engineering Research Board
Openalex Percentile: Top 23%
Asymmetric Hydrogenation and Catalysis
DOISourceOpenAlex
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From Esters to Benzodiazepines: A Two-Step Nickel–Iridium Catalytic Pathway via Amide Intermediates — P. Madhavan Nair, Boopathy Gnanaprakasam, et al. · Organic Letters (2026) | TGRS Research Map | TGRS