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^*

^*此作品的通讯作者

化学与分子工程学院

East China Normal University

科研成果: 期刊稿件 › 文章 › 同行评审

1 引用（Scopus）

摘要

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.

源语言	英语
页（从-至）	8542-8549
页数	8
期刊	Journal of Organic Chemistry
卷	90
期	25
DOI	https://doi.org/10.1021/acs.joc.5c00497
出版状态	已出版 - 27 6月 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.\}",

note = "Publisher Copyright: {\textcopyright} 2025 American Chemical Society.",

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

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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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