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2013•Organic LettersRequires access

Regioselectivity in the Nucleophile Trapping of Arynes: The Electronic and Steric Effects of Nucleophiles and Substituents

Rajdip Karmakar, Sang Young Yun, Kung-Pern Wang, Daesung Lee

Open publisher page 73 citations

Abstract

The regioselectivity in nucleophile trapping is investigated with arynes generated directly from bis-1,3-diynes. The regioselectivity is profoundly influenced by not only the nature of nucleophiles but also the substituents on the arynes, which is the consequence of both the unfavorable steric interaction between the incoming nucleophile and the nearby substituent and the inherent electronic bias induced by different substituents on the arynes.

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What this paper is about

The regioselectivity in nucleophile trapping is investigated with arynes generated directly from bis-1,3-diynes. The regioselectivity is profoundly influenced by not only the nature of nucleophiles but also the substituents on the arynes, which is the consequence of both the unfavorable steric interaction between the incoming nucleophile and the nearby substituent and the inherent electronic bias induced by different substituents on the arynes.

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Available abstract

The regioselectivity in nucleophile trapping is investigated with arynes generated directly from bis-1,3-diynes. The regioselectivity is profoundly influenced by not only the nature of nucleophiles but also the substituents on the arynes, which is the consequence of both the unfavorable steric interaction between the incoming nucleophile and the nearby substituent and the inherent electronic bias induced by different substituents on the arynes.

Key concepts: Aryne, Nucleophile, Regioselectivity, Chemistry, Steric effects, Substituent, Electronic effect, Trapping

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