共 47 条
Nickel-Catalyzed Reductive Methylation of Alkyl Halides and Acid Chlorides with Methyl p-Tosylate
被引:90
作者:

Liang, Zhuye
论文数: 0 引用数: 0
h-index: 0
机构:
Zhengzhou Univ, Coll Chem & Mol Engn, Zhengzhou 450001, Peoples R China Zhengzhou Univ, Coll Chem & Mol Engn, Zhengzhou 450001, Peoples R China

Xue, Weichao
论文数: 0 引用数: 0
h-index: 0
机构:
Shanghai Univ, Dept Chem, Shanghai 200444, Peoples R China Zhengzhou Univ, Coll Chem & Mol Engn, Zhengzhou 450001, Peoples R China

Lin, Kunhua
论文数: 0 引用数: 0
h-index: 0
机构:
Shanghai Univ, Dept Chem, Shanghai 200444, Peoples R China Zhengzhou Univ, Coll Chem & Mol Engn, Zhengzhou 450001, Peoples R China

Gong, Hegui
论文数: 0 引用数: 0
h-index: 0
机构:
Shanghai Univ, Dept Chem, Shanghai 200444, Peoples R China Zhengzhou Univ, Coll Chem & Mol Engn, Zhengzhou 450001, Peoples R China
机构:
[1] Zhengzhou Univ, Coll Chem & Mol Engn, Zhengzhou 450001, Peoples R China
[2] Shanghai Univ, Dept Chem, Shanghai 200444, Peoples R China
关键词:
CROSS-COUPLING REACTIONS;
ARYL HALIDES;
ALKYLBORONIC ESTERS;
GRIGNARD-REAGENTS;
KETONE FORMATION;
NI;
BORYLATION;
BROMIDES;
BOND;
CARBOXYLATION;
D O I:
10.1021/ol502682q
中图分类号:
O62 [有机化学];
学科分类号:
070303 ;
081704 ;
摘要:
Methylation of unactivated alkyl halides and acid chlorides under Ni-catalyzed reductive coupling conditions led to efficient formation of methylated alkanes and ketones using methyl p-methyl tosylate as the methylation reagent. Moderate to excellent coupling yields as well as excellent functional group tolerance were observed under the present mild and easy-to-operate reaction conditions.
引用
收藏
页码:5620 / 5623
页数:4
相关论文
共 47 条
[1]
The Methylation Effect in Medicinal Chemistry
[J].
Barreiro, Eliezer J.
;
Kuemmerle, Arthur E.
;
Fraga, Carlos A. M.
.
CHEMICAL REVIEWS,
2011, 111 (09)
:5215-5246

Barreiro, Eliezer J.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Fed Rio de Janeiro, Fac Farm, Lab Avaliacao & Sintese Subst Bioat LASSBio, CCS, BR-21941902 Rio De Janeiro, Brazil
Univ Fed Rio de Janeiro, Inst Ciencias Biomed, Programa Posgrad Farmacol & Quim Med, BR-21941902 Rio De Janeiro, Brazil
Univ Fed Rio de Janeiro, Inst Quim, Programa Posgrad Quim, BR-21941902 Rio De Janeiro, Brazil Univ Fed Rio de Janeiro, Fac Farm, Lab Avaliacao & Sintese Subst Bioat LASSBio, CCS, BR-21941902 Rio De Janeiro, Brazil

Kuemmerle, Arthur E.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Fed Rio de Janeiro, Fac Farm, Lab Avaliacao & Sintese Subst Bioat LASSBio, CCS, BR-21941902 Rio De Janeiro, Brazil
Univ Fed Rio de Janeiro, Inst Quim, Programa Posgrad Quim, BR-21941902 Rio De Janeiro, Brazil Univ Fed Rio de Janeiro, Fac Farm, Lab Avaliacao & Sintese Subst Bioat LASSBio, CCS, BR-21941902 Rio De Janeiro, Brazil

Fraga, Carlos A. M.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Fed Rio de Janeiro, Fac Farm, Lab Avaliacao & Sintese Subst Bioat LASSBio, CCS, BR-21941902 Rio De Janeiro, Brazil
Univ Fed Rio de Janeiro, Inst Ciencias Biomed, Programa Posgrad Farmacol & Quim Med, BR-21941902 Rio De Janeiro, Brazil
Univ Fed Rio de Janeiro, Inst Quim, Programa Posgrad Quim, BR-21941902 Rio De Janeiro, Brazil Univ Fed Rio de Janeiro, Fac Farm, Lab Avaliacao & Sintese Subst Bioat LASSBio, CCS, BR-21941902 Rio De Janeiro, Brazil
[2]
Mechanism and Selectivity in Nickel-Catalyzed Cross-Electrophile Coupling of Aryl Halides with Alkyl Halides
[J].
Biswas, Soumik
;
Weix, Daniel J.
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2013, 135 (43)
:16192-16197

Biswas, Soumik
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Rochester, Dept Chem, Rochester, NY 14627 USA Univ Rochester, Dept Chem, Rochester, NY 14627 USA

Weix, Daniel J.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Rochester, Dept Chem, Rochester, NY 14627 USA Univ Rochester, Dept Chem, Rochester, NY 14627 USA
[3]
Ni-Catalyzed Carboxylation of C(sp2)- and C(sp3)-O Bonds with CO2
[J].
Correa, Arkaitz
;
Leon, Thierry
;
Martin, Ruben
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2014, 136 (03)
:1062-1069

Correa, Arkaitz
论文数: 0 引用数: 0
h-index: 0
机构:
Inst Chem Res Catalonia ICIQ, Tarragona 43007, Spain Inst Chem Res Catalonia ICIQ, Tarragona 43007, Spain

Leon, Thierry
论文数: 0 引用数: 0
h-index: 0
机构:
Inst Chem Res Catalonia ICIQ, Tarragona 43007, Spain Inst Chem Res Catalonia ICIQ, Tarragona 43007, Spain

Martin, Ruben
论文数: 0 引用数: 0
h-index: 0
机构:
Inst Chem Res Catalonia ICIQ, Tarragona 43007, Spain
Catalan Inst Res & Adv Studies ICREA, Barcelona 08010, Spain Inst Chem Res Catalonia ICIQ, Tarragona 43007, Spain
[4]
Ni-Catalyzed Reductive Allylation of Unactivated Alkyl Halides with Allylic Carbonates
[J].
Dai, Yijing
;
Wu, Fan
;
Zang, Zhenhua
;
You, Hengzhi
;
Gong, Hegui
.
CHEMISTRY-A EUROPEAN JOURNAL,
2012, 18 (03)
:808-812

Dai, Yijing
论文数: 0 引用数: 0
h-index: 0
机构:
Shanghai Univ, Dept Chem, Shanghai 200444, Peoples R China Shanghai Univ, Dept Chem, Shanghai 200444, Peoples R China

Wu, Fan
论文数: 0 引用数: 0
h-index: 0
机构:
Shanghai Univ, Dept Chem, Shanghai 200444, Peoples R China Shanghai Univ, Dept Chem, Shanghai 200444, Peoples R China

Zang, Zhenhua
论文数: 0 引用数: 0
h-index: 0
机构:
Shanghai Univ, Dept Chem, Shanghai 200444, Peoples R China Shanghai Univ, Dept Chem, Shanghai 200444, Peoples R China

You, Hengzhi
论文数: 0 引用数: 0
h-index: 0
机构:
Shanghai Univ, Dept Chem, Shanghai 200444, Peoples R China Shanghai Univ, Dept Chem, Shanghai 200444, Peoples R China

Gong, Hegui
论文数: 0 引用数: 0
h-index: 0
机构:
Shanghai Univ, Dept Chem, Shanghai 200444, Peoples R China Shanghai Univ, Dept Chem, Shanghai 200444, Peoples R China
[5]
Nickel-Catalyzed Coupling Reactions of Alkyl Electrophiles, Including Unactivated Tertiary Halides, To Generate Carbon-Boron Bonds
[J].
Dudnik, Alexander S.
;
Fu, Gregory C.
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2012, 134 (25)
:10693-10697

Dudnik, Alexander S.
论文数: 0 引用数: 0
h-index: 0
机构:
MIT, Dept Chem, Cambridge, MA 02139 USA MIT, Dept Chem, Cambridge, MA 02139 USA

Fu, Gregory C.
论文数: 0 引用数: 0
h-index: 0
机构:
MIT, Dept Chem, Cambridge, MA 02139 USA MIT, Dept Chem, Cambridge, MA 02139 USA
[6]
PREPARATION OF ARYL, ALKYNYL, AND VINYL ORGANOCOPPER COMPOUNDS BY THE OXIDATIVE ADDITION OF ZEROVALENT COPPER TO CARBON-HALOGEN BONDS
[J].
EBERT, GW
;
RIEKE, RD
.
JOURNAL OF ORGANIC CHEMISTRY,
1988, 53 (19)
:4482-4488

EBERT, GW
论文数: 0 引用数: 0
h-index: 0
机构:
UNIV NEBRASKA, DEPT CHEM, LINCOLN, NE 68588 USA UNIV NEBRASKA, DEPT CHEM, LINCOLN, NE 68588 USA

RIEKE, RD
论文数: 0 引用数: 0
h-index: 0
机构:
UNIV NEBRASKA, DEPT CHEM, LINCOLN, NE 68588 USA UNIV NEBRASKA, DEPT CHEM, LINCOLN, NE 68588 USA
[7]
Cross-Electrophile Coupling: Principles of Reactivity and Selectivity
[J].
Everson, Daniel A.
;
Weix, Daniel J.
.
JOURNAL OF ORGANIC CHEMISTRY,
2014, 79 (11)
:4793-4798

Everson, Daniel A.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA Univ Rochester, Dept Chem, Rochester, NY 14627 USA

Weix, Daniel J.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Rochester, Dept Chem, Rochester, NY 14627 USA Univ Rochester, Dept Chem, Rochester, NY 14627 USA
[8]
Nickel-Catalyzed Reductive Cross-Coupling of Aryl Halides with Alkyl Halides
[J].
Everson, Daniel A.
;
Shrestha, Ruja
;
Weix, Daniel J.
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2010, 132 (03)
:920-+

Everson, Daniel A.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Rochester, Dept Chem, Rochester, NY 14627 USA Univ Rochester, Dept Chem, Rochester, NY 14627 USA

Shrestha, Ruja
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Rochester, Dept Chem, Rochester, NY 14627 USA Univ Rochester, Dept Chem, Rochester, NY 14627 USA

Weix, Daniel J.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Rochester, Dept Chem, Rochester, NY 14627 USA Univ Rochester, Dept Chem, Rochester, NY 14627 USA
[9]
Asymmetric nickel-catalyzed negishi cross-couplings of secondary α-bromo amides with organozinc reagents
[J].
Fischer, C
;
Fu, GC
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2005, 127 (13)
:4594-4595

Fischer, C
论文数: 0 引用数: 0
h-index: 0
机构:
MIT, Dept Chem, Cambridge, MA 02139 USA MIT, Dept Chem, Cambridge, MA 02139 USA

Fu, GC
论文数: 0 引用数: 0
h-index: 0
机构:
MIT, Dept Chem, Cambridge, MA 02139 USA MIT, Dept Chem, Cambridge, MA 02139 USA
[10]
Catalysts for cross-coupling reactions with non-activated alkyl halides
[J].
Frisch, AC
;
Beller, M
.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2005, 44 (05)
:674-688

Frisch, AC
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Rostock, Leibniz Inst Organ Katalyse, D-18055 Rostock, Germany Univ Rostock, Leibniz Inst Organ Katalyse, D-18055 Rostock, Germany

Beller, M
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Rostock, Leibniz Inst Organ Katalyse, D-18055 Rostock, Germany Univ Rostock, Leibniz Inst Organ Katalyse, D-18055 Rostock, Germany