Au(I) /Brønsted Acid Relay-Catalyzed Benzannulation Reaction of Alkynylbenzaldehydes and Styrenes for the Synthesis of Substituted Naphthalenes

We report herein an Au(I) /Brønsted acid relay-catalyzed tandem benzannulation reaction of alkynylbenzaldehydes and styrenes for the synthesis of substituted naphthalenes. This reaction sequence involves Au(I)-catalyzed alkyne cycloisomerization, oxa-[4 + 2]-cycloaddition, α-ketol rearrangement, and aromatization to access substituted naphthalenes in moderate-to-good yields. The resulting substituted naphthalenes are further subjected to Brønsted acid catalysis, promoting Friedel-Crafts reactions to form chrysene derivatives in excellent yields.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-04-01
DOI
https://doi.org/10.1021/acs.joc.4c03186
Citations
2
Primary Topic
Catalytic Alkyne Reactions
Type
article
Field-Weighted Citation Impact
1.87

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article

Au(I) /Brønsted Acid Relay-Catalyzed Benzannulation Reaction of Alkynylbenzaldehydes and Styrenes for the Synthesis of Substituted Naphthalenes

Yuanzhen Xu, Yun Li, Shaolong Zheng
2 citations
The Journal of Organic Chemistry
Catalytic Alkyne Reactions
1.87
article

Au(I) /Brønsted Acid Relay-Catalyzed Benzannulation Reaction of Alkynylbenzaldehydes and Styrenes for the Synthesis of Substituted Naphthalenes

Yuanzhen Xu, Yun Li, Shaolong Zheng
article en
2 citations

Abstract

We report herein an Au(I) /Brønsted acid relay-catalyzed tandem benzannulation reaction of alkynylbenzaldehydes and styrenes for the synthesis of substituted naphthalenes. This reaction sequence involves Au(I)-catalyzed alkyne cycloisomerization, oxa-[4 + 2]-cycloaddition, α-ketol rearrangement, and aromatization to access substituted naphthalenes in moderate-to-good yields. The resulting substituted naphthalenes are further subjected to Brønsted acid catalysis, promoting Friedel-Crafts reactions to form chrysene derivatives in excellent yields.

The Journal of Organic ChemistryVol. 90(14)
State Key Laboratory of Applied Organic Chemistry, Lanzhou University (CN), Northwest A&F University (CN)
National Natural Science Foundation of China, Fundamental Research Funds for the Central Universities, Science and Technology Program of Gansu Province
Clean water and sanitation
Openalex Percentile: Top 17%
Catalytic Alkyne Reactions
1.87
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Au(I) /Brønsted Acid Relay-Catalyzed Benzannulation Reaction of Alkynylbenzaldehydes and Styrenes for the Synthesis of Substituted Naphthalenes — Yuanzhen Xu, Yun Li, et al. · The Journal of Organic Chemistry (2025) | TGRS Research Map | TGRS