Nickel N-Heterocyclic Carbene Catalyst for Cross-Coupling of Neopentyl Arenesulfonates with Methyl and Primary Alkyl Grignard Reagents

被引：31

作者：

Kim, Chul-Bae ^{[1
]}

Jo, Hyunjong ^{[1
]}

Ahn, Bo-Kyoung ^{[1
]}

Kim, Chang Keun ^{[1
]}

Park, Kwangyong ^{[1
]}

机构：

[1] Chung Ang Univ, Sch Chem Engn & Mat Sci, Seoul 156756, South Korea

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 74卷 / 24期

关键词：

UNACTIVATED ARYL CHLORIDES; C BOND FORMATION; ROOM-TEMPERATURE; NHC LIGANDS; RESTRICTED FLEXIBILITY; ARYLBORONIC ACIDS; COMPLEXES; AMINATION; BROMIDES; HALIDES;

D O I：

10.1021/jo902151h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nickel N-heterocyclic carbene (NHC) catalytic system prepared in Situ by the reaction of Ni(acac)(2) with NHC precursor efficiently catalyzed the cross-coupling reaction of alkoxysulfonylarenes with methyl, neopentyl, and benzyl Grignard reagents at ambient temperature.

引用

页码：9566 / 9569

页数：4

共 50 条

[1] Synthesis of Terphenyls and Quaterphenyls via the Nickel N-Heterocyclic Carbene-Catalyzed Cross-Coupling of Neopentyl Arenesulfonates with Aryl Grignard Reagents
Jo, Hyunjong
Kim, Chul-Bae
Ryoo, Tae-Yong
Ahn, Bo-Kyoung
Park, Kwangyong
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2010, 31 (12): : 3749 - 3754
[2] Highly Active [Pd(μ-Cl)(Cl)(NHC)]2 (NHC = N-Heterocyclic Carbene) in the Cross-Coupling of Grignard Reagents with Aryl Chlorides
Hartmann, Caroline E.
Nolan, Steven P.
Cazin, Catherine S. J.
ORGANOMETALLICS, 2009, 28 (09) : 2915 - 2919
[3] An N-heterocyclic carbene-based nickel catalyst for the Kumada-Tamao-Corriu coupling of aryl bromides and tertiary alkyl Grignard reagents
Ando, Shin
Mawatari, Mai
Matsunaga, Hirofumi
Ishizuka, Tadao
TETRAHEDRON LETTERS, 2016, 57 (30) : 3287 - 3290
[4] Iron Fluoride/N-Heterocyclic Carbene Catalyzed Cross Coupling between Deactivated Aryl Chlorides and Alkyl Grignard Reagents with or without β-Hydrogens
Agata, Ryosuke
Iwamoto, Takahiro
Nakagawa, Naohisa
Isozaki, Katsuhiro
Hatakeyama, Takuji
Takaya, Hikaru
Nakamura, Masaharu
SYNTHESIS-STUTTGART, 2015, 47 (12): : 1733 - 1740
[5] Cross-Coupling of Non-activated Chloroalkanes with Aryl Grignard Reagents in the Presence of Iron/N-Heterocyclic Carbene Catalysts
Ghorai, Sujit K.
Jin, Masayoshi
Hatakeyama, Takuji
Nakamura, Masaharu
ORGANIC LETTERS, 2012, 14 (04) : 1066 - 1069
[6] An N-heterocyclic carbene based MOF catalyst for Sonogashira cross-coupling reaction
Ezugwu, Chizoba I.
Mousavi, Bibimaryam
Asrafa, Md. Ali
Mehta, Akshay
Vardhan, Harsh
Verpoort, Francis
CATALYSIS SCIENCE & TECHNOLOGY, 2016, 6 (07) : 2050 - 2054
[7] Cross-Coupling of ArX with ArMgBr Catalyzed by N-Heterocyclic Carbene-Based Nickel Complexes
Guo, Wang-Jun
Wang, Zhong-Xia
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (03): : 1054 - 1061
[8] Cross-Coupling of Nonactivated Alkyl Halides with Alkynyl Grignard Reagents: A Nickel Pincer Complex as the Catalyst
Vechorkin, Oleg
Godinat, Aurelien
Scopelliti, Rosario
Hu, Xile
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (49) : 11777 - 11781
[9] Efficient nickel/N-heterocyclic carbene catalyzed C-S cross-coupling
Guan, Pei
Cao, Changsheng
Liu, Yun
Li, Yunfei
He, Pan
Chen, Qian
Liu, Gang
Shi, Yanhui
TETRAHEDRON LETTERS, 2012, 53 (45) : 5987 - 5992
[10] Nickel-Catalyzed Aromatic Cross-Coupling Difluoromethylation of Grignard Reagents with Difluoroiodomethane
Motohashi, Hirotaka
Mikami, Koichi
ORGANIC LETTERS, 2018, 20 (17) : 5340 - 5343

← 1 2 3 4 5 →