Aromatic Homo-Nazarov-Type Cyclization of Benzonorcaradienes: Stereoselective Synthesis of Hydrochrysenes

Caiyun An; Hongyan Bi; Sunewang R. Wang

doi:10.1021/acs.joc.3c00052

Aromatic Homo-Nazarov-Type Cyclization of Benzonorcaradienes: Stereoselective Synthesis of Hydrochrysenes

Caiyun An
, Hongyan Bi
, 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

5 引用（Scopus）

摘要

Formal homo-Nazarov cyclization of benzonorcaradienes produced by intramolecular hydroarylation of arylated alkynylcyclopropanes promoted by TfOH has been described, providing stereoselective access to highly substituted hydrochrysenes. An unprecedented 1,2-acyl migration occurred for the 2-heteroaroyl substrates, thus giving the same products as their 3-heteroaroyl analogs. Moreover, these products could be readily oxidized by air to fully π-conjugated chrysenes after decarboxylation.

源语言	英语
页（从-至）	2670-2674
页数	5
期刊	Journal of Organic Chemistry
卷	88
期	4
DOI	https://doi.org/10.1021/acs.joc.3c00052
出版状态	已出版 - 17 2月 2023

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title = "Aromatic Homo-Nazarov-Type Cyclization of Benzonorcaradienes: Stereoselective Synthesis of Hydrochrysenes",

abstract = "Formal homo-Nazarov cyclization of benzonorcaradienes produced by intramolecular hydroarylation of arylated alkynylcyclopropanes promoted by TfOH has been described, providing stereoselective access to highly substituted hydrochrysenes. An unprecedented 1,2-acyl migration occurred for the 2-heteroaroyl substrates, thus giving the same products as their 3-heteroaroyl analogs. Moreover, these products could be readily oxidized by air to fully π-conjugated chrysenes after decarboxylation.",

author = "Caiyun An and Hongyan Bi and Wang, \{Sunewang R.\}",

note = "Publisher Copyright: {\textcopyright} 2023 American Chemical Society.",

year = "2023",

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doi = "10.1021/acs.joc.3c00052",

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T1 - Aromatic Homo-Nazarov-Type Cyclization of Benzonorcaradienes

T2 - Stereoselective Synthesis of Hydrochrysenes

AU - An, Caiyun

AU - Bi, Hongyan

AU - Wang, Sunewang R.

PY - 2023/2/17

Y1 - 2023/2/17

N2 - Formal homo-Nazarov cyclization of benzonorcaradienes produced by intramolecular hydroarylation of arylated alkynylcyclopropanes promoted by TfOH has been described, providing stereoselective access to highly substituted hydrochrysenes. An unprecedented 1,2-acyl migration occurred for the 2-heteroaroyl substrates, thus giving the same products as their 3-heteroaroyl analogs. Moreover, these products could be readily oxidized by air to fully π-conjugated chrysenes after decarboxylation.

AB - Formal homo-Nazarov cyclization of benzonorcaradienes produced by intramolecular hydroarylation of arylated alkynylcyclopropanes promoted by TfOH has been described, providing stereoselective access to highly substituted hydrochrysenes. An unprecedented 1,2-acyl migration occurred for the 2-heteroaroyl substrates, thus giving the same products as their 3-heteroaroyl analogs. Moreover, these products could be readily oxidized by air to fully π-conjugated chrysenes after decarboxylation.

UR - https://www.scopus.com/pages/publications/85147963863

U2 - 10.1021/acs.joc.3c00052

DO - 10.1021/acs.joc.3c00052

M3 - 文章

AN - SCOPUS:85147963863

SN - 0022-3263

VL - 88

SP - 2670

EP - 2674

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 4

ER -

Aromatic Homo-Nazarov-Type Cyclization of Benzonorcaradienes: Stereoselective Synthesis of Hydrochrysenes

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