One‐Pot Transition‐Metal‐Free Synthesis of Polysubstituted Fused Benzene Derivatives from Methyl Enol Ethers and Alkynes

Ahmad, Sarwat Asma Ziya and Khan, Faiz Ahmed (2022) One‐Pot Transition‐Metal‐Free Synthesis of Polysubstituted Fused Benzene Derivatives from Methyl Enol Ethers and Alkynes. ChemistrySelect, 7 (33). ISSN 2365-6549

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Abstract

A mild and transition-metal-free one-pot strategy is established to prepare polysubstituted naphthalene and phenanthrene derivatives from methyl enol ethers (MEE) with alkynes. Significantly, this protocol is promoted by boron trifluoride diethyl etherate (BF3⋅Et2O) at room temperature. A wide variety of diversely functionalized naphthalene and phenanthrene derivatives were obtained in good to excellent yields. A plausible mechanism involving a spiro quinonoid intermediate is proposed. Due to fluorescent nature of naphthalene, selected compounds were screened for the solvatochromism study. Notably, positive solvatochromism effect was observed in the case of nitro-substituted naphthalene derivative (3 h) with respect to different polarity of solvents. © 2022 Wiley-VCH GmbH.

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IITH Creators:

IITH Creators	ORCiD
Khan, Faiz Ahmed	UNSPECIFIED

Item Type:

Article

Additional Information:

We gratefully acknowledge the Science and Engineering Research Board (SERB, EMR/2017/003484), India, for financial support. S. A. Z. A thanks DST-INSPIRE, India, for the award of PhD fellowship.

Uncontrolled Keywords:

benzannulation; methyl enol ethers; naphthalenes; phenanthrenes; solvatochromism

Subjects:

Chemistry

Divisions:

Department of Chemistry

Depositing User:

. LibTrainee 2021

Date Deposited:

27 Sep 2022 06:30

Last Modified:

27 Sep 2022 06:31