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^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

East China Normal University

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

5 Scopus citations

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.

Original language	English
Pages (from-to)	2670-2674
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	88
Issue number	4
DOIs	https://doi.org/10.1021/acs.joc.3c00052
State	Published - 17 Feb 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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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

Abstract

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