Regiodivergent Annulation Reactions of Chalcones to Indenones and Indanones with C1 Reagents

Xinchi Gong; Sunewang R. Wang

doi:10.1021/acs.joc.5c00497

Regiodivergent Annulation Reactions of Chalcones to Indenones and Indanones with C1 Reagents

Xinchi Gong
, Sunewang R. Wang^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

East China Normal University

Research output: Contribution to journal › Article › peer-review

Abstract

One-pot direct regiodivergent annulations of chalcones, as exemplified by the drug metochalcone and a bioactive dichloro-substituted chalcone with a quinoline ring, to indanones and indenones are conveniently achieved with single-carbon reagent Kukhtin-Ramirez adducts. A Cs₂CO₃-promoted unusual selective cleavage of the cyclopropyl C-C bond distal to the strong carbonyl acceptor, further driven to completion by follow-up regiodivergent annulations via Pd(OAc)₂-catalyzed Heck reaction or Cs₂CO₃-mediated S_NAr process, is key for the success.

Original language	English
Pages (from-to)	8542-8549
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	90
Issue number	25
DOIs	https://doi.org/10.1021/acs.joc.5c00497
State	Published - 27 Jun 2025

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title = "Regiodivergent Annulation Reactions of Chalcones to Indenones and Indanones with C1 Reagents",

abstract = "One-pot direct regiodivergent annulations of chalcones, as exemplified by the drug metochalcone and a bioactive dichloro-substituted chalcone with a quinoline ring, to indanones and indenones are conveniently achieved with single-carbon reagent Kukhtin-Ramirez adducts. A Cs2CO3-promoted unusual selective cleavage of the cyclopropyl C-C bond distal to the strong carbonyl acceptor, further driven to completion by follow-up regiodivergent annulations via Pd(OAc)2-catalyzed Heck reaction or Cs2CO3-mediated SNAr process, is key for the success.",

author = "Xinchi Gong and Wang, \{Sunewang R.\}",

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year = "2025",

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doi = "10.1021/acs.joc.5c00497",

language = "英语",

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journal = "Journal of Organic Chemistry",

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T1 - Regiodivergent Annulation Reactions of Chalcones to Indenones and Indanones with C1 Reagents

AU - Gong, Xinchi

AU - Wang, Sunewang R.

PY - 2025/6/27

Y1 - 2025/6/27

N2 - One-pot direct regiodivergent annulations of chalcones, as exemplified by the drug metochalcone and a bioactive dichloro-substituted chalcone with a quinoline ring, to indanones and indenones are conveniently achieved with single-carbon reagent Kukhtin-Ramirez adducts. A Cs2CO3-promoted unusual selective cleavage of the cyclopropyl C-C bond distal to the strong carbonyl acceptor, further driven to completion by follow-up regiodivergent annulations via Pd(OAc)2-catalyzed Heck reaction or Cs2CO3-mediated SNAr process, is key for the success.

AB - One-pot direct regiodivergent annulations of chalcones, as exemplified by the drug metochalcone and a bioactive dichloro-substituted chalcone with a quinoline ring, to indanones and indenones are conveniently achieved with single-carbon reagent Kukhtin-Ramirez adducts. A Cs2CO3-promoted unusual selective cleavage of the cyclopropyl C-C bond distal to the strong carbonyl acceptor, further driven to completion by follow-up regiodivergent annulations via Pd(OAc)2-catalyzed Heck reaction or Cs2CO3-mediated SNAr process, is key for the success.

UR - https://www.scopus.com/pages/publications/105008303455

U2 - 10.1021/acs.joc.5c00497

DO - 10.1021/acs.joc.5c00497

M3 - 文章

AN - SCOPUS:105008303455

SN - 0022-3263

VL - 90

SP - 8542

EP - 8549

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 25

ER -

Regiodivergent Annulation Reactions of Chalcones to Indenones and Indanones with C1 Reagents

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