共 78 条
Rh(i)- and Rh(ii)-catalyzed C-H alkylation of benzylamines with alkenes and its application in flow chemistry
被引:10
作者:

Das, Amrita
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Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan

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[1] Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan
关键词:
RHODIUM-CATALYZED ALKYLATION;
AROMATIC AMIDES;
BOND FUNCTIONALIZATION;
POSSIBLE GENERATION;
OXIDATIVE ADDITION;
DIRECTING GROUPS;
CARBENE COMPLEX;
ACTIVATION;
DERIVATIVES;
PICOLINAMIDE;
D O I:
10.1039/d0sc05813k
中图分类号:
O6 [化学];
学科分类号:
0703 ;
摘要:
The Rh-catalyzed C-H alkylation of benzylamines with alkenes using a picolinamide derivative as a directing group is reported. Both Rh(i) and Rh(ii) complexes can be used as active catalysts for this transformation. In addition, a flow set up was designed to successfully mimic this process under flow conditions. Several examples are presented under flow conditions and it was confirmed that a flow process is advantageous over a batch process. Deuterium labelling experiments were performed to elucidate the mechanism of the reaction, and the results indicated a possible carbene mechanism for this C-H alkylation process.
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页码:3202 / 3209
页数:8
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[1]
The Nickel(II)-Catalyzed Direct Benzylation, Allylation, Alkylation, and Methylation of C-H Bonds in Aromatic Amides Containing an 8-Aminoquinoline Moiety as the Directing Group
[J].
Aihara, Yoshinori
;
Wuelbern, Jendrik
;
Chatani, Naoto
.
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN,
2015, 88 (03)
:438-446

Aihara, Yoshinori
论文数: 0 引用数: 0
h-index: 0
机构:
Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan

Wuelbern, Jendrik
论文数: 0 引用数: 0
h-index: 0
机构:
Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan

论文数: 引用数:
h-index:
机构:
[2]
Nickel-Catalyzed Direct Alkylation of C-H Bonds in Benzamides and Acrylamides with Functionalized Alkyl Halides via Bidentate-Chelation Assistance
[J].
Aihara, Yoshinori
;
Chatani, Naoto
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2013, 135 (14)
:5308-5311

Aihara, Yoshinori
论文数: 0 引用数: 0
h-index: 0
机构:
Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan

论文数: 引用数:
h-index:
机构:
[3]
A Perspective on Continuous Flow Chemistry in the Pharmaceutical Industry
[J].
Baumann, Marcus
;
Moody, Thomas S.
;
Smyth, Megan
;
Wharry, Scott
.
ORGANIC PROCESS RESEARCH & DEVELOPMENT,
2020, 24 (10)
:1802-1813

Baumann, Marcus
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Coll Dublin, Sci Ctr, Sch Chem, Dublin 4, Ireland Almac Grp Ltd, Craigavon BT63 5QD, England

Moody, Thomas S.
论文数: 0 引用数: 0
h-index: 0
机构:
Almac Grp Ltd, Craigavon BT63 5QD, England
Arran Chem Co, Roscommon N37 DN24, Ireland Almac Grp Ltd, Craigavon BT63 5QD, England

Smyth, Megan
论文数: 0 引用数: 0
h-index: 0
机构:
Almac Grp Ltd, Craigavon BT63 5QD, England Almac Grp Ltd, Craigavon BT63 5QD, England

Wharry, Scott
论文数: 0 引用数: 0
h-index: 0
机构:
Almac Grp Ltd, Craigavon BT63 5QD, England Almac Grp Ltd, Craigavon BT63 5QD, England
[4]
Emerging Trends in Flow Chemistry and Applications to the Pharmaceutical Industry
[J].
Bogdan, Andrew R.
;
Dombrowski, Amanda W.
.
JOURNAL OF MEDICINAL CHEMISTRY,
2019, 62 (14)
:6422-6468

Bogdan, Andrew R.
论文数: 0 引用数: 0
h-index: 0
机构:
AbbVie Inc, Discovery Chem & Technol, 1 North Waukegan Rd, N Chicago, IL 60064 USA AbbVie Inc, Discovery Chem & Technol, 1 North Waukegan Rd, N Chicago, IL 60064 USA

Dombrowski, Amanda W.
论文数: 0 引用数: 0
h-index: 0
机构:
AbbVie Inc, Discovery Chem & Technol, 1 North Waukegan Rd, N Chicago, IL 60064 USA AbbVie Inc, Discovery Chem & Technol, 1 North Waukegan Rd, N Chicago, IL 60064 USA
[5]
Continuous flow palladium-catalyzed trifluoromethylthiolation of C-H bonds
[J].
Bouchard, Alexanne
;
Kairouz, Vanessa
;
Manneveau, Maxime
;
Xiong, Heng-Ying
;
Besset, Tatiana
;
Pannecoucke, Xavier
;
Lebel, Helene
.
JOURNAL OF FLOW CHEMISTRY,
2019, 9 (01)
:9-12

Bouchard, Alexanne
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Montreal, Dept Chem, POB 6128, Montreal, PQ, Canada
Univ Montreal, Continuous Flow Synth Lab, POB 6128, Montreal, PQ, Canada Univ Montreal, Dept Chem, POB 6128, Montreal, PQ, Canada

Kairouz, Vanessa
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Montreal, Dept Chem, POB 6128, Montreal, PQ, Canada
Univ Montreal, Continuous Flow Synth Lab, POB 6128, Montreal, PQ, Canada Univ Montreal, Dept Chem, POB 6128, Montreal, PQ, Canada

Manneveau, Maxime
论文数: 0 引用数: 0
h-index: 0
机构:
Normandie Univ, INSA Rouen, CNRS, UNIROUEN,COBRA,UMR 6014, F-76000 Rouen, France Univ Montreal, Dept Chem, POB 6128, Montreal, PQ, Canada

Xiong, Heng-Ying
论文数: 0 引用数: 0
h-index: 0
机构:
Normandie Univ, INSA Rouen, CNRS, UNIROUEN,COBRA,UMR 6014, F-76000 Rouen, France Univ Montreal, Dept Chem, POB 6128, Montreal, PQ, Canada

Besset, Tatiana
论文数: 0 引用数: 0
h-index: 0
机构:
Normandie Univ, INSA Rouen, CNRS, UNIROUEN,COBRA,UMR 6014, F-76000 Rouen, France Univ Montreal, Dept Chem, POB 6128, Montreal, PQ, Canada

Pannecoucke, Xavier
论文数: 0 引用数: 0
h-index: 0
机构:
Normandie Univ, INSA Rouen, CNRS, UNIROUEN,COBRA,UMR 6014, F-76000 Rouen, France Univ Montreal, Dept Chem, POB 6128, Montreal, PQ, Canada

Lebel, Helene
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Montreal, Dept Chem, POB 6128, Montreal, PQ, Canada
Univ Montreal, Continuous Flow Synth Lab, POB 6128, Montreal, PQ, Canada Univ Montreal, Dept Chem, POB 6128, Montreal, PQ, Canada
[6]
Indirect ortho functionalization of substituted toluenes through ortho olefination of N,N-dimethylbenzylamines tuned by the acidity of reaction conditions
[J].
Cai, Guixin
;
Fu, Ye
;
Li, Yizhou
;
Wan, Xiaobing
;
Shi, Zhangjie
.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
2007, 129 (24)
:7666-7673

Cai, Guixin
论文数: 0 引用数: 0
h-index: 0
机构: Peking Univ, BNLMS, PKU Green Chem Ctr, Coll Chem, Beijing 100871, Peoples R China

Fu, Ye
论文数: 0 引用数: 0
h-index: 0
机构: Peking Univ, BNLMS, PKU Green Chem Ctr, Coll Chem, Beijing 100871, Peoples R China

Li, Yizhou
论文数: 0 引用数: 0
h-index: 0
机构: Peking Univ, BNLMS, PKU Green Chem Ctr, Coll Chem, Beijing 100871, Peoples R China

Wan, Xiaobing
论文数: 0 引用数: 0
h-index: 0
机构: Peking Univ, BNLMS, PKU Green Chem Ctr, Coll Chem, Beijing 100871, Peoples R China

Shi, Zhangjie
论文数: 0 引用数: 0
h-index: 0
机构:
Peking Univ, BNLMS, PKU Green Chem Ctr, Coll Chem, Beijing 100871, Peoples R China Peking Univ, BNLMS, PKU Green Chem Ctr, Coll Chem, Beijing 100871, Peoples R China
[7]
A bis(thiophosphinoyl)methylene ruthenium carbene complex:: Synthesis, X-ray crystal structure, and DFT calculations of its thermally promoted reverse α-hydride migration process
[J].
Cantat, T
;
Demange, M
;
Mézailles, N
;
Ricard, L
;
Jean, Y
;
Le Floch, P
.
ORGANOMETALLICS,
2005, 24 (20)
:4838-4841

Cantat, T
论文数: 0 引用数: 0
h-index: 0
机构:
Ecole Polytech, Dept Chim, CNRS, Lab Heteroelements & Coordinat,UMR 7653,DCPH, F-91128 Palaiseau, France Ecole Polytech, Dept Chim, CNRS, Lab Heteroelements & Coordinat,UMR 7653,DCPH, F-91128 Palaiseau, France

Demange, M
论文数: 0 引用数: 0
h-index: 0
机构:
Ecole Polytech, Dept Chim, CNRS, Lab Heteroelements & Coordinat,UMR 7653,DCPH, F-91128 Palaiseau, France Ecole Polytech, Dept Chim, CNRS, Lab Heteroelements & Coordinat,UMR 7653,DCPH, F-91128 Palaiseau, France

Mézailles, N
论文数: 0 引用数: 0
h-index: 0
机构:
Ecole Polytech, Dept Chim, CNRS, Lab Heteroelements & Coordinat,UMR 7653,DCPH, F-91128 Palaiseau, France Ecole Polytech, Dept Chim, CNRS, Lab Heteroelements & Coordinat,UMR 7653,DCPH, F-91128 Palaiseau, France

Ricard, L
论文数: 0 引用数: 0
h-index: 0
机构:
Ecole Polytech, Dept Chim, CNRS, Lab Heteroelements & Coordinat,UMR 7653,DCPH, F-91128 Palaiseau, France Ecole Polytech, Dept Chim, CNRS, Lab Heteroelements & Coordinat,UMR 7653,DCPH, F-91128 Palaiseau, France

Jean, Y
论文数: 0 引用数: 0
h-index: 0
机构:
Ecole Polytech, Dept Chim, CNRS, Lab Heteroelements & Coordinat,UMR 7653,DCPH, F-91128 Palaiseau, France Ecole Polytech, Dept Chim, CNRS, Lab Heteroelements & Coordinat,UMR 7653,DCPH, F-91128 Palaiseau, France

Le Floch, P
论文数: 0 引用数: 0
h-index: 0
机构:
Ecole Polytech, Dept Chim, CNRS, Lab Heteroelements & Coordinat,UMR 7653,DCPH, F-91128 Palaiseau, France Ecole Polytech, Dept Chim, CNRS, Lab Heteroelements & Coordinat,UMR 7653,DCPH, F-91128 Palaiseau, France
[8]
The Use of a Rhodium Catalyst/8-Aminoquinoline Directing Group in the C-H Alkylation of Aromatic Amides with Alkenes: Possible Generation of a Carbene Intermediate from an Alkene
[J].
Chatani, Naoto
.
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN,
2018, 91 (02)
:211-222

论文数: 引用数:
h-index:
机构:
[9]
Transition metal-catalyzed C-H bond functionalizations by the use of diverse directing groups
[J].
Chen, Zhengkai
;
Wang, Binjie
;
Zhang, Jitan
;
Yu, Wenlong
;
Liu, Zhanxiang
;
Zhang, Yuhong
.
ORGANIC CHEMISTRY FRONTIERS,
2015, 2 (09)
:1107-1295

Chen, Zhengkai
论文数: 0 引用数: 0
h-index: 0
机构:
Zhejiang Univ, Dept Chem, ZJU NHU United R&D Ctr, Hangzhou 310027, Zhejiang, Peoples R China Zhejiang Univ, Dept Chem, ZJU NHU United R&D Ctr, Hangzhou 310027, Zhejiang, Peoples R China

Wang, Binjie
论文数: 0 引用数: 0
h-index: 0
机构:
Zhejiang Univ, Dept Chem, ZJU NHU United R&D Ctr, Hangzhou 310027, Zhejiang, Peoples R China Zhejiang Univ, Dept Chem, ZJU NHU United R&D Ctr, Hangzhou 310027, Zhejiang, Peoples R China

Zhang, Jitan
论文数: 0 引用数: 0
h-index: 0
机构:
Zhejiang Univ, Dept Chem, ZJU NHU United R&D Ctr, Hangzhou 310027, Zhejiang, Peoples R China Zhejiang Univ, Dept Chem, ZJU NHU United R&D Ctr, Hangzhou 310027, Zhejiang, Peoples R China

Yu, Wenlong
论文数: 0 引用数: 0
h-index: 0
机构:
Zhejiang Univ, Dept Chem, ZJU NHU United R&D Ctr, Hangzhou 310027, Zhejiang, Peoples R China Zhejiang Univ, Dept Chem, ZJU NHU United R&D Ctr, Hangzhou 310027, Zhejiang, Peoples R China

Liu, Zhanxiang
论文数: 0 引用数: 0
h-index: 0
机构:
Zhejiang Univ, Dept Chem, ZJU NHU United R&D Ctr, Hangzhou 310027, Zhejiang, Peoples R China Zhejiang Univ, Dept Chem, ZJU NHU United R&D Ctr, Hangzhou 310027, Zhejiang, Peoples R China

Zhang, Yuhong
论文数: 0 引用数: 0
h-index: 0
机构:
Zhejiang Univ, Dept Chem, ZJU NHU United R&D Ctr, Hangzhou 310027, Zhejiang, Peoples R China
Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China Zhejiang Univ, Dept Chem, ZJU NHU United R&D Ctr, Hangzhou 310027, Zhejiang, Peoples R China
[10]
Arylation of Pyridines via Suzuki-Miyaura Cross-Coupling and Pyridine-Directed C-H Activation Using a Continuous-Flow Approach
[J].
Christakakou, Maria
;
Schoen, Michael
;
Schnuerch, Michael
;
Mihovilovic, Marko D.
.
SYNLETT,
2013, 24 (18)
:2411-2418

Christakakou, Maria
论文数: 0 引用数: 0
h-index: 0
机构:
Vienna Univ Technol, Inst Appl Synthet Chem, A-1060 Vienna, Austria Vienna Univ Technol, Inst Appl Synthet Chem, A-1060 Vienna, Austria

Schoen, Michael
论文数: 0 引用数: 0
h-index: 0
机构:
Vienna Univ Technol, Inst Appl Synthet Chem, A-1060 Vienna, Austria Vienna Univ Technol, Inst Appl Synthet Chem, A-1060 Vienna, Austria

Schnuerch, Michael
论文数: 0 引用数: 0
h-index: 0
机构:
Vienna Univ Technol, Inst Appl Synthet Chem, A-1060 Vienna, Austria Vienna Univ Technol, Inst Appl Synthet Chem, A-1060 Vienna, Austria

Mihovilovic, Marko D.
论文数: 0 引用数: 0
h-index: 0
机构:
Vienna Univ Technol, Inst Appl Synthet Chem, A-1060 Vienna, Austria Vienna Univ Technol, Inst Appl Synthet Chem, A-1060 Vienna, Austria