Efficient synthesis of racemic and chiral alkenyl sulfoxides by palladium-catalyzed Suzuki coupling

Gisela Mancha; Ana B. Cuenca; Nuria Rodríguez; Mercedes Medio-Simón; Gregorio Asensio

doi:10.1016/j.tet.2010.06.050

Efficient synthesis of racemic and chiral alkenyl sulfoxides by palladium-catalyzed Suzuki coupling

Gisela Mancha
, Ana B. Cuenca
, Nuria Rodríguez
, Mercedes Medio-Simón^*
, Gregorio Asensio

^*Autor corresponent d’aquest treball

Producció científica: Article en revista indexada › Article › Avaluat per experts

6 Cites (Scopus)

Resum

Alkenyl sulfoxide derivatives are obtained in high yields through a palladium-catalyzed Suzuki/Miyaura cross-coupling reaction of racemic and chiral 1-halo sulfoxides with aryl and alkenyl boronic acids. Chiral substrates react with no loss of optical purity and high optical yields. The reaction takes place with different palladium catalysts, such as Pd(PPh₃)₄ or Pd(OAc)₂/DABCO. Although nitrogen ligands like DABCO lead to an active palladium catalyst, they are less effective than the phosphine ones.

Idioma original	Anglès
Pàgines (de-a)	6901-6905
Nombre de pàgines	5
Revista	Tetrahedron
Volum	66
Número	34
DOIs	https://doi.org/10.1016/j.tet.2010.06.050
Estat de la publicació	Publicada - 21 d’ag. 2010
Publicat externament	Sí

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10.1016/j.tet.2010.06.050

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@article{5e4113fd47ec4420adef9d5becd8c783,

title = "Efficient synthesis of racemic and chiral alkenyl sulfoxides by palladium-catalyzed Suzuki coupling",

abstract = "Alkenyl sulfoxide derivatives are obtained in high yields through a palladium-catalyzed Suzuki/Miyaura cross-coupling reaction of racemic and chiral 1-halo sulfoxides with aryl and alkenyl boronic acids. Chiral substrates react with no loss of optical purity and high optical yields. The reaction takes place with different palladium catalysts, such as Pd(PPh3)4 or Pd(OAc)2/DABCO. Although nitrogen ligands like DABCO lead to an active palladium catalyst, they are less effective than the phosphine ones.",

keywords = "Boronic acids, Cross-coupling, Palladium, Sulfoxides, Suzuki reaction",

author = "Gisela Mancha and Cuenca, \{Ana B.\} and Nuria Rodr{\'i}guez and Mercedes Medio-Sim{\'o}n and Gregorio Asensio",

note = "Funding Information: Financial support by the Spanish Direcci{\'o}n General de Investigaci{\'o}n Cient{\'i}fica y T{\'e}cnica Consolider Ingenio 2010 ( CSD2007-00006 ), ( CTQ2007-65720 ) and the Generalitat Valenciana (G.M. grant) is gratefully acknowledged. We gratefully acknowledge SCSIE (Universidad de Valencia) for access to the instrumental facilities. ",

year = "2010",

month = aug,

day = "21",

doi = "10.1016/j.tet.2010.06.050",

language = "English",

volume = "66",

pages = "6901--6905",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd.",

number = "34",

}

TY - JOUR

T1 - Efficient synthesis of racemic and chiral alkenyl sulfoxides by palladium-catalyzed Suzuki coupling

AU - Mancha, Gisela

AU - Cuenca, Ana B.

AU - Rodríguez, Nuria

AU - Medio-Simón, Mercedes

AU - Asensio, Gregorio

N1 - Funding Information: Financial support by the Spanish Dirección General de Investigación Científica y Técnica Consolider Ingenio 2010 ( CSD2007-00006 ), ( CTQ2007-65720 ) and the Generalitat Valenciana (G.M. grant) is gratefully acknowledged. We gratefully acknowledge SCSIE (Universidad de Valencia) for access to the instrumental facilities.

PY - 2010/8/21

Y1 - 2010/8/21

N2 - Alkenyl sulfoxide derivatives are obtained in high yields through a palladium-catalyzed Suzuki/Miyaura cross-coupling reaction of racemic and chiral 1-halo sulfoxides with aryl and alkenyl boronic acids. Chiral substrates react with no loss of optical purity and high optical yields. The reaction takes place with different palladium catalysts, such as Pd(PPh3)4 or Pd(OAc)2/DABCO. Although nitrogen ligands like DABCO lead to an active palladium catalyst, they are less effective than the phosphine ones.

AB - Alkenyl sulfoxide derivatives are obtained in high yields through a palladium-catalyzed Suzuki/Miyaura cross-coupling reaction of racemic and chiral 1-halo sulfoxides with aryl and alkenyl boronic acids. Chiral substrates react with no loss of optical purity and high optical yields. The reaction takes place with different palladium catalysts, such as Pd(PPh3)4 or Pd(OAc)2/DABCO. Although nitrogen ligands like DABCO lead to an active palladium catalyst, they are less effective than the phosphine ones.

KW - Boronic acids

KW - Cross-coupling

KW - Palladium

KW - Sulfoxides

KW - Suzuki reaction

UR - https://www.scopus.com/pages/publications/77955467524

UR - https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=pure_univeritat_ramon_llull&SrcAuth=WosAPI&KeyUT=WOS:000280953500030&DestLinkType=FullRecord&DestApp=WOS_CPL

U2 - 10.1016/j.tet.2010.06.050

DO - 10.1016/j.tet.2010.06.050

M3 - Article

AN - SCOPUS:77955467524

SN - 0040-4020

VL - 66

SP - 6901

EP - 6905

JO - Tetrahedron

JF - Tetrahedron

IS - 34

ER -

Efficient synthesis of racemic and chiral alkenyl sulfoxides by palladium-catalyzed Suzuki coupling

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