Oxygen-promoted Pd(II) catalysis for the coupling of organoboron compounds and olefins

被引:146
作者
Jung, YC [1 ]
Mishra, RK [1 ]
Yoon, CH [1 ]
Jung, KW [1 ]
机构
[1] Univ S Florida, Dept Chem, Tampa, FL 33620 USA
关键词
D O I
10.1021/ol034458s
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reported herein is a mild and efficient Pd(II) catalysis, leading to the formation of carbon-carbon bonds between a broad spectrum of organoboron compounds and alkenes. Molecular oxygen was employed to reoxidize the resultant Pd(0) species back to Pd(II) during catalytic cycles. This oxygen protocol promoted the desired Pd(II) catalysis, whereas it retarded competing Pd(0) catalytic pathways such as Heck or Suzuki couplings.
引用
收藏
页码:2231 / 2234
页数:4
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共 46 条
[21]   Palladium-catalyzed synthesis of biaryls from arylzinc compounds using N-chlorosuccinimide or oxygen as an oxidant [J].
Hossain, KM ;
Kameyama, T ;
Shibata, T ;
Takagi, K .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2001, 74 (12) :2415-2420
[22]   Synthesis of heterocycles using the intramolecular Heck reaction involving a 'formal' anti-elimination process [J].
Ikeda, M ;
El Bialy, SAA ;
Yakura, T .
HETEROCYCLES, 1999, 51 (08) :1957-1970
[23]   Palladium(II)-catalyzed cyclization of olefinic tosylamides [J].
Larock, RC ;
Hightower, TR ;
Hasvold, LA ;
Peterson, KP .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) :3584-3585
[24]   Palladium(II)-catalyzed phenylation of unsaturated compounds using phenylantimony chlorides under air [J].
Matoba, K ;
Motofusa, S ;
Cho, CS ;
Ohe, K ;
Uemura, S .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 574 (01) :3-10
[25]   Cyclic carbopalladation. A versatile synthetic methodology for the construction of cyclic organic compounds [J].
Negishi, EI ;
Coperet, C ;
Ma, SM ;
Liou, SY ;
Liu, F .
CHEMICAL REVIEWS, 1996, 96 (01) :365-393
[26]   A novel diarylation reaction of alkynes by using aryltributylstannane in the presence of palladium catalyst [J].
Oda, H ;
Morishita, M ;
Fugami, K ;
Sano, H ;
Kosugi, M .
CHEMISTRY LETTERS, 1996, (09) :811-812
[27]   Palladium(II)-catalyzed aryl coupling of triarylbismuthines under air [J].
Ohe, T ;
Tanaka, T ;
Kuroda, M ;
Cho, CS ;
Ohe, K ;
Uemura, S .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1999, 72 (08) :1851-1855
[28]   Oxidative dimerization: Pd(II) catalysis in the presence of oxygen using aqueous media [J].
Parrish, JP ;
Jung, YC ;
Floyd, RJ ;
Jung, KW .
TETRAHEDRON LETTERS, 2002, 43 (44) :7899-7902
[29]   Mild and efficient aryl-alkenyl coupling via Pd(II) catalysis in the presence of oxygen or Cu(II) oxidants [J].
Parrish, JP ;
Jung, YC ;
Shin, SI ;
Jung, KW .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (20) :7127-7130
[30]   Palladium-catalyzed oxidation of primary and secondary allylic and benzylic alcohols [J].
Peterson, KP ;
Larock, RC .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (10) :3185-3189