Direct Coupling of Naphthalene and Sulfonimides Promoted by DDQ and Blue Light

被引:20
作者
Sakakibara, Yota [1 ,2 ]
Ito, Eri [1 ,2 ]
Kawakami, Takahiro [1 ,2 ]
Yamada, Shuya [1 ,2 ]
Murakami, Kei [1 ,2 ]
Itami, Kenichiro [1 ,2 ,3 ]
机构
[1] Nagoya Univ, Inst Transformat Biomol WPI ITbM, Chikusa Ku, Nagoya, Aichi 4648602, Japan
[2] Nagoya Univ, Grad Sch Sci, Chikusa Ku, Nagoya, Aichi 4648602, Japan
[3] Nagoya Univ, Itami Mol Nanocarbon Project, JST ERATO, Chikusa Ku, Nagoya, Aichi 4648602, Japan
关键词
Aromatic C-H amination; DDQ; Blue light; C-H AMINATION; IMIDATION; ARENES; AMIDATION; HETEROARENES; CATALYSIS; MILD;
D O I
10.1246/cl.170321
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Aromatic C-H amination chemistry has attracted significant attention as an alternative to conventional amination of aryl halides. Among C-H amination reactions, dehydrogenative coupling of arenes and N-H reagents represents an ideal transformation because prefunctionalization steps of arenes or aminating reagents are not required. Herein, we report direct C-H/N-H coupling between naphthalene and sulfonimides mediated by 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) as a photosensitizer under irradiation of blue light.
引用
收藏
页码:1014 / 1016
页数:3
相关论文
共 36 条
[1]   N-Acyloxyphthalimides as Nitrogen Radical Precursors in the Visible Light Photocatalyzed Room Temperature C-H Amination of Arenes and Heteroarenes [J].
Allen, Laura J. ;
Cabrera, Pablo J. ;
Lee, Melissa ;
Sanford, Melanie S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (15) :5607-5610
[2]  
Boursalian GB, 2016, NAT CHEM, V8, P810, DOI [10.1038/nchem.2529, 10.1038/NCHEM.2529]
[3]   Pd-Catalyzed Aryl C-H Imidation with Arene as the Limiting Reagent [J].
Boursalian, Gregory B. ;
Ngai, Ming-Yu ;
Hojczyk, Katarzyna N. ;
Ritter, Tobias .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (36) :13278-13281
[4]   Visible light C-H amidation of heteroarenes with benzoyl azides [J].
Brachet, E. ;
Ghosh, T. ;
Ghosh, I. ;
Koenig, B. .
CHEMICAL SCIENCE, 2015, 6 (02) :987-992
[5]   Recent advances in the transition metal-catalyzed twofold oxidative C-H bond activation strategy for C-C and C-N bond formation [J].
Cho, Seung Hwan ;
Kim, Ji Young ;
Kwak, Jaesung ;
Chang, Sukbok .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :5068-5083
[6]   Catalytic C-H functionalization by metal carbenoid and nitrenoid insertion [J].
Davies, Huw M. L. ;
Manning, James R. .
NATURE, 2008, 451 (7177) :417-424
[7]   A Mild, Ferrocene-Catalyzed C-H Imidation of (Hetero)Arenes [J].
Foo, Klement ;
Sella, Eran ;
Thome, Isabelle ;
Eastgate, Martin D. ;
Baran, Phil S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (14) :5279-5282
[8]   Cu-Catalyzed aromatic C-H imidation with N-fluorobenzenesulfonimide: mechanistic details and predictive models [J].
Haines, Brandon E. ;
Kawakami, Takahiro ;
Kuwata, Keiko ;
Murakami, Kei ;
Itami, Kenichiro ;
Musaev, Djamaladdin G. .
CHEMICAL SCIENCE, 2017, 8 (02) :988-1001
[9]   Making carbon-nitrogen bonds in biological and chemical synthesis [J].
Hili, Ryan ;
Yudin, Andrei K. .
NATURE CHEMICAL BIOLOGY, 2006, 2 (06) :284-287
[10]   Catalytic Dehydrogenative C-H Imidation of Arenes Enabled by Photo-generated Hole Donation to Sulfonimide [J].
Ito, Eri ;
Fukushima, Tomohiro ;
Kawakami, Takahiro ;
Murakami, Kei ;
Itami, Kenichiro .
CHEM, 2017, 2 (03) :383-392