Addition reaction of arylboronic acids to aldehydes and α,β-unsaturated carbonyl compounds catalyzed by conventional palladium complexes in the presence of chloroform

被引：37

作者：

Yamamoto, Tetsuya ^{[1
]}

Iizuka, Michiko ^{[1
]}

Takenaka, Hiroto ^{[1
]}

Ohta, Tetsuo ^{[1
]}

Ito, Yoshihiko ^{[1
]}

机构：

[1] Doshisha Univ, Fac Life & Med Sci, Dept Biomed Informat, Kyoto 6100394, Japan

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2009年 / 694卷 / 9-10期

关键词：

Palladium; Addition reaction; Organoboronic acid; Aldehyde; alpha; beta-Unsaturated carbonyl compounds; Chloroform; CONJUGATE ADDITION; ASYMMETRIC 1,4-ADDITION; ORGANOBORONIC ACIDS; PALLADIUM(II)-CATALYZED ADDITION; ALKENYLBORONIC ACIDS; AROMATIC-ALDEHYDES; COUPLING REACTIONS; BORONIC ACIDS; ARYLATION; ARYL;

D O I：

10.1016/j.jorganchem.2008.12.032

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Arylboronic acids react with aldehydes and alpha,beta-unsaturated carbonyl compounds in the presence of a base and a catalytic amount of a palladium(0) complex with chloroform, affording the corresponding addition products in good yields, and chiral benzhydrol was obtained with up to 43% e. e. using (S,S)-bppm as a ligand. General palladium complexes have no catalytic activity without chloroform. Because chloroform is essential for this reaction, these reactions would be promoted by dichloromethylpalladium(II) species. (C) 2008 Elsevier B.V. All rights reserved.

引用

页码：1325 / 1332

页数：8

共 66 条

[1] RETRACTED: Asymmetric Ni-catalyzed arylation of aromatic aldehydes with arylboroxines (Retracted Article) [J].

Arao, Takafumi ;

Kondo, Kazuhiro ;

Aoyama, Toyohiko .

TETRAHEDRON, 2007, 63 (24) :5261-5264

[2] Asymmetric synthesis of diarylmethanols: Development of a hemilabile phosphorus ligand based on the concept of conformational control [J].

Arao, Takafumi ;

Suzuki, Kiyoto ;

Kondo, Kazuhiro ;

Aoyama, Toyobiko .

SYNTHESIS-STUTTGART, 2006, (22) :3809-3814

[3] RESEARCH ON ANTIBACTERIAL AND ANTIFUNGAL AGENTS .16. SYNTHESIS AND ANTIFUNGAL ACTIVITIES OF 1-[ALPHA-(1-NAPHTHYL)BENZYL]IMIDAZOLE DERIVATIVES AND RELATED 2-NAPHTHYL ISOMERS [J].

ARTICO, M ;

STEFANCICH, G ;

SILVESTRI, R ;

MASSA, S ;

APUZZO, G ;

ARTICO, M ;

SIMONETTI, G .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1992, 27 (07) :693-699

[4] A NEW CATALYTIC ACTIVITY OF ANTIMONY(III) CHLORIDE IN PALLADIUM(0)-CATALYZED CONJUGATE ADDITION OF AROMATICS TO ALPHA,BETA-UNSATURATED KETONES AND ALDEHYDES WITH SODIUM TETRAPHENYLBORATE AND ARYLBORONIC ACIDS [J].

CHO, CS ;

MOTOFUSA, S ;

OHE, K ;

UEMURA, S .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (04) :883-888

[5] Selected patented cross-coupling reaction technologies [J].

Corbet, Jean-Pierre ;

Mignani, Gerard .

CHEMICAL REVIEWS, 2006, 106 (07) :2651-2710

[6] Diastereoselective synthesis of arylglycine derivatives by cationic Palladium(II)-Catalyzed addition of arylboronic acids to N-tert-Butanesulfinyl imino esters [J].

Dai, Huixiong ;

Lu, Xiyan .

ORGANIC LETTERS, 2007, 9 (16) :3077-3080

[7] SUBSTITUENT EFFECTS, ELECTRONIC TRANSMISSION AND STRUCTURAL DEPENDENCE OF PI DELOCALIZATION AS STUDIED WITH PARA-FLUOROPHENYL TAG [J].

DAYAL, SK ;

EHRENSON, S ;

TAFT, RW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (26) :9113-9122

[8] Palladium-catalyzed conjugate addition of organosiloxanes to α,β-unsaturated carbonyl compounds and nitroalkenes [J].

Denmark, SE ;

Amishiro, N .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (18) :6997-7003

[9] Enantioselective Rh-catalyzed arylation of N-tosylarylimines with arylboronic acids [J].

Duan, Hai-Feng ;

Jia, Yi-Xia ;

Wang, Li-Xin ;

Zhou, Qi-Lin .

ORGANIC LETTERS, 2006, 8 (12) :2567-2569

[10] Rhodium-catalyzed carbon-carbon bond forming reactions of organometallic compounds [J].

Fagnou, K ;

Lautens, M .

CHEMICAL REVIEWS, 2003, 103 (01) :169-196

← 1 2 3 4 5 6 7 →