Electrochemical domino sulfonylation/dearomative ipso-annulation of 2-alkynyl biaryls to access spiro(indenyl)cyclohexadienones

IF 2.5 3区 化学 Q2 CHEMISTRY, ORGANIC European Journal of Organic Chemistry Pub Date : 2024-10-02 DOI:10.1002/ejoc.202400990
Chada Raji Reddy, Karna Nair, Puthiya P Vinaya, Uprety Ajaykumar, Rene Gree
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Abstract

Herein, we present an efficient strategy for the synthesis of spiro(indenyl)cyclohexadienones through radical-promoted reaction of 2-alkynyl biaryls with sodium sulfinates under electrochemical conditions. The reaction involves sulfonylation and dearomative ipso-cyclisation in a domino fashion. This approach features the use of readily accessible precursors, wide functional group tolerance and external oxidant-free reaction conditions. The practicality of the method was also illustrated by scale-up reaction and further diversification of the product
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电化学多米诺磺酰化反应/2-炔基双芳基异烷基化反应生成螺(茚基)环己二烯酮
在此,我们提出了一种在电化学条件下通过 2-炔基双芳族化合物与亚硫酸钠的自由基促进反应合成螺(茚基)环己二烯酮的高效策略。该反应以多米诺方式进行磺酰化和脱芳基异环化。这种方法的特点是使用容易获得的前体、广泛的官能团耐受性和外部无氧化剂反应条件。该方法的实用性还体现在反应规模的扩大和产物的进一步多样化上。
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来源期刊
CiteScore
5.40
自引率
3.60%
发文量
752
审稿时长
1 months
期刊介绍: The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry: Liebigs Annalen Bulletin des Sociétés Chimiques Belges Bulletin de la Société Chimique de France Gazzetta Chimica Italiana Recueil des Travaux Chimiques des Pays-Bas Anales de Química Chimika Chronika Revista Portuguesa de Química ACH—Models in Chemistry Polish Journal of Chemistry.
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