Gold(l)-catalyzed intermodular oxyarylation of alkynes: Unexpected regiochemistry in the alkylation of arenes

Ana B. Cuenca; Sergi Montserrat; Kabir M. Hossain; Gisela Mancha; Agustí Lledós; Mercedes Medio-Simón; Gregoři Ujaque; Gregorio Asensio

doi:10.1021/ol9020578

Gold(l)-catalyzed intermodular oxyarylation of alkynes: Unexpected regiochemistry in the alkylation of arenes

Ana B. Cuenca, Sergi Montserrat, Kabir M. Hossain, Gisela Mancha, Agustí Lledós, Mercedes Medio-Simón, Gregoři Ujaque, Gregorio Asensio^*

^*Autor/a de correspondencia de este trabajo

Producción científica: Artículo en revista indizada › Artículo › revisión exhaustiva

120 Citas (Scopus)

Resumen

The reaction between acetylenes and sulfoxides, studied as a test case for gold-catalyzed intermolecular addition, provides the oxyarylation compounds 3 In good yields. Unpredictably, In all cases a single regioisomer arising from the electrophilic aromatic alkylation at the position adjacent to the sulfur atom Is obtained Instead of the expected Friedel-Crafts regioisomer. A new concerted mechanism based on DFT calculations Is proposed to account for the products In this lntermolecular gold(l)-catalyzed reaction.

Idioma original	Inglés
Páginas (desde-hasta)	4906-4909
Número de páginas	4
Publicación	Organic Letters
Volumen	11
N.º	21
DOI	https://doi.org/10.1021/ol9020578
Estado	Publicada - 5 nov 2009
Publicado de forma externa	Sí

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10.1021/ol9020578

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title = "Gold(l)-catalyzed intermodular oxyarylation of alkynes: Unexpected regiochemistry in the alkylation of arenes",

abstract = "The reaction between acetylenes and sulfoxides, studied as a test case for gold-catalyzed intermolecular addition, provides the oxyarylation compounds 3 In good yields. Unpredictably, In all cases a single regioisomer arising from the electrophilic aromatic alkylation at the position adjacent to the sulfur atom Is obtained Instead of the expected Friedel-Crafts regioisomer. A new concerted mechanism based on DFT calculations Is proposed to account for the products In this lntermolecular gold(l)-catalyzed reaction.",

keywords = "Homogeneous gold catalysis, Au catalysis, Pi-acids, Cycloisomerization, Generation, Diversity, Platinum, Cascade",

author = "Cuenca, {Ana B.} and Sergi Montserrat and Hossain, {Kabir M.} and Gisela Mancha and Agust{\'i} Lled{\'o}s and Mercedes Medio-Sim{\'o}n and Grego{\v r}i Ujaque and Gregorio Asensio",

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T1 - Gold(l)-catalyzed intermodular oxyarylation of alkynes

T2 - Unexpected regiochemistry in the alkylation of arenes

AU - Cuenca, Ana B.

AU - Montserrat, Sergi

AU - Hossain, Kabir M.

AU - Mancha, Gisela

AU - Lledós, Agustí

AU - Medio-Simón, Mercedes

AU - Ujaque, Gregoři

AU - Asensio, Gregorio

PY - 2009/11/5

Y1 - 2009/11/5

N2 - The reaction between acetylenes and sulfoxides, studied as a test case for gold-catalyzed intermolecular addition, provides the oxyarylation compounds 3 In good yields. Unpredictably, In all cases a single regioisomer arising from the electrophilic aromatic alkylation at the position adjacent to the sulfur atom Is obtained Instead of the expected Friedel-Crafts regioisomer. A new concerted mechanism based on DFT calculations Is proposed to account for the products In this lntermolecular gold(l)-catalyzed reaction.

AB - The reaction between acetylenes and sulfoxides, studied as a test case for gold-catalyzed intermolecular addition, provides the oxyarylation compounds 3 In good yields. Unpredictably, In all cases a single regioisomer arising from the electrophilic aromatic alkylation at the position adjacent to the sulfur atom Is obtained Instead of the expected Friedel-Crafts regioisomer. A new concerted mechanism based on DFT calculations Is proposed to account for the products In this lntermolecular gold(l)-catalyzed reaction.

KW - Homogeneous gold catalysis

KW - Au catalysis

KW - Pi-acids

KW - Cycloisomerization

KW - Generation

KW - Diversity

KW - Platinum

KW - Cascade

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JO - Organic Letters

JF - Organic Letters

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ER -

Gold(l)-catalyzed intermodular oxyarylation of alkynes: Unexpected regiochemistry in the alkylation of arenes

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