Direct Cobalt-Catalyzed Conjugate Addition of Functionalized Aryl Halides and Triflates: A New Strategy for the Conjugate Addition onto Methyl Vinyl Ketone

被引：18

作者：

Amatore, Muriel ^{[1
]}

Gosmini, Corinne ^{[1
]}

机构：

[1] Ecole Polytech, Lab Heteroelements & Coordinat, CNRS, F-91128 Palaiseau, France

来源：

SYNLETT | 2009年 / 07期

关键词：

aryl halides; catalysis; cobalt; direct conjugate addition; methyl vinyl ketone; CROSS-COUPLING REACTIONS; BOND-FORMING REACTIONS; GRIGNARD-REAGENTS; SAMARIUM(II) IODIDE; OXIDATIVE ADDITION; ORGANIC HALIDES; ALKYL-HALIDES; PALLADIUM(0) COMPLEXES; ACTIVATED OLEFINS; PHENYL IODIDE;

D O I：

10.1055/s-0028-1088117

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient cobalt-catalyzed method for the direct con jugate addition of functionalized aryl halides or triflates onto methyl vinyl ketone is described. The experimentally simple procedure relies on the use of a catalytic system consisting of CoBr2(Bpy) and zinc and does not require the preformation of a stoichiometric organometallic species. The approach described herein displays considerable functional-group compatibility at good to excellent yields.

引用

页码：1073 / 1076

页数：4

共 34 条

[21] CONJUGATE ADDITION OF B-ALKENYL-9-BORABICYCLO[3.3.1]NONANES TO METHYL VINYL KETONE - CONVENIENT SYNTHESIS OF GAMMA, DELTA-UNSATURATE KETONES
JACOB, P
BROWN, HC
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (24) : 7832 - 7833
[22] A Strategy Enabling Enantioselective Direct Conjugate Addition of Inert Aryl Methane Nucleophiles to Enals with a Chiral Amine Catalyst under Mild Conditions
Li, Tengfei
Zhu, Jin
Wu, Deyan
Li, Xiangmin
Wang, Sinan
Li, Hao
Li, Jian
Wang, Wei
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (28) : 9147 - 9150
[23] Synthesis of Propargylamines via Michael Addition Using Methyl Vinyl Ketone Derivatives, 1-Alkynes, and Secondary Amines Catalyzed by Copper (I) Halides
Udaykumar, Bantu
Periasamy, Mariappan
ACS OMEGA, 2019, 4 (25): : 21587 - 21595
[24] THE DIRECT FORMATION OF FUNCTIONALIZED ALKYL(ARYL)ZINC HALIDES BY OXIDATIVE ADDITION OF HIGHLY REACTIVE ZINC WITH ORGANIC HALIDES AND THEIR REACTIONS WITH ACID-CHLORIDES, ALPHA,BETA-UNSATURATED KETONES, AND ALLYLIC, ARYL, AND VINYL HALIDES
ZHU, L
WEHMEYER, RM
RIEKE, RD
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (04): : 1445 - 1453
[25] LEWIS ACID-CATALYZED MICHAEL-TYPE ADDITION - A NEW REGIOSELECTIVE AND DIASTEREOSELECTIVE ANNULATION METHOD USING METHYL VINYL KETONE
DUHAMEL, P
DUJARDIN, G
HENNEQUIN, L
POIRIER, JM
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (03): : 387 - 396
[26] DIRECT FORMATION OF FUNCTIONALIZED ALKYLCOPPER REAGENTS FROM ALKYL-HALIDES USING ACTIVATED COPPER - CONJUGATE ADDITION-REACTIONS WITH 2-CYCLOHEXEN-1-ONE
WEHMEYER, RM
RIEKE, RD
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (22): : 5056 - 5057
[27] Hydroxyl group-directed, tartaric acid-catalyzed synthesis of meta-functionalized aryl ethers and phenols through domino conjugate addition/aromatization of para-quinols
Chen, Guo-Shu
Li, Jia-Hui
Chen, Shu-Jie
Lin, Wen-Xia
Ren, Hai
Deng, Dong-Sheng
Liu, Yun-Lin
ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (24) : 6851 - 6856
[28] Synthesis of new chiral aryl diphosphite ligands derived from pyranoside backbone of monosacharides and their application in copper-catalyzed asymmetric conjugate addition of diethylzinc to cyclic enones
Wang, LL
Li, YM
Yip, CW
Qiu, LQ
Zhou, ZY
Chan, ASC
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (08) : 947 - 953
[29] CONJUGATE ADDITION VS VINYLIC SUBSTITUTION IN PALLADIUM-CATALYZED REACTION OF ARYL HALIDES WITH BETA-SUBSTITUTED-ALPHA,BETA-ENONES AND BETA-SUBSTITUTED-ALPHA,BETA-ENALS
AMORESE, A
ARCADI, A
BERNOCCHI, E
CACCHI, S
CERRINI, S
FEDELI, W
ORTAR, G
TETRAHEDRON, 1989, 45 (03) : 813 - 828
[30] Tunable 1,3-lithium shift of propargylic/allenylic lithiums formed by conjugate addition of 4-aryl-3-butyn-1-enes with organolithiums and the subsequent transmetalation/Pd(O)-catalyzed coupling reaction with aryl halides
Ma, SM
He, QW
Jin, X
SYNLETT, 2005, (03) : 514 - 516

← 1 2 3 4 →