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

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 inter...

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Bibliographic Details
Published in:Organic letters 2014-01, Vol.16 (1), p.6-9
Main Authors: Karmakar, Rajdip, Yun, Sang Young, Wang, Kung-Pern, Lee, Daesung
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol403237z