Regioselective Three-Component Synthesis of Vicinal Diamines via 1,2-Diamination of Styrenes

被引:26
作者
Cao, Jie [1 ,2 ]
Lv, Daqi [1 ,2 ]
Yu, Fei [2 ]
Chiou, Mong-Feng [2 ]
Li, Yajun [2 ]
Bao, Hongli [2 ]
机构
[1] Fuzhou Univ, Coll Chem, Fuzhou 350108, Fujian, Peoples R China
[2] Chinese Acad Sci, Ctr Excellence Mol Synth, Fujian Inst Res Struct Matter,State Key Lab Struc, Key Lab Coal Ethylene Glycol & Its Related Techno, Fuzhou 350002, Fujian, Peoples R China
关键词
CATALYTIC ASYMMETRIC DIAMINATION; METAL-FREE DIAMINATION; CONJUGATED DIENES; INTERMOLECULAR 1,2-DIAMINATION; PD(0)-CATALYZED DIAMINATION; TERMINAL OLEFINS; ALKENES; DIFUNCTIONALIZATION; FUNCTIONALIZATION; AZODICARBOXYLATE;
D O I
10.1021/acs.orglett.1c00898
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The vicinal diamine motif plays a significant role in natural products, drug design, and organic synthesis, and development of synthetic methods for the synthesis of diamines is a long-standing interest. Herein, we report a regioselective intermolecular three-component vicinal diamination of styrenes with acetonitrile and azodicarboxylates. The diamination products can be produced in moderate to excellent yields via the Ritter reaction. Synthetic applications and theoretical studies of this reaction have been conducted.
引用
收藏
页码:3184 / 3189
页数:6
相关论文
共 79 条
[1]   Pd(II)-catalyzed intermolecular 1,2-diamination of conjugated dienes [J].
Bar, GLJ ;
Lloyd-Jones, GC ;
Booker-Milburn, KI .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (20) :7308-7309
[2]   The mitsunobu reaction: Origin, mechanism, improvements, and applications [J].
But, Tracy Yuen Sze ;
Toy, Patrick H. .
CHEMISTRY-AN ASIAN JOURNAL, 2007, 2 (11) :1340-1355
[3]   Practical and stereoselective electrocatalytic 1,2-diamination of alkenes [J].
Cai, Chen-Yan ;
Shu, Xiao-Min ;
Xu, Hai-Chao .
NATURE COMMUNICATIONS, 2019, 10 (1)
[4]  
Cardona F, 2009, NAT CHEM, V1, P269, DOI [10.1038/NCHEM.256, 10.1038/nchem.256]
[5]   Metal-free diamination of alkenes employing bromide catalysis [J].
Chavez, Patricia ;
Kirsch, Jonathan ;
Hoevelmann, Claas H. ;
Streuff, Jan ;
Martinez-Belmonte, Marta ;
Escudero-Adan, Eduardo C. ;
Martin, Eddy ;
Muniz, Kilian .
CHEMICAL SCIENCE, 2012, 3 (07) :2375-2382
[6]   SYNTHESIS OF DIOXOBIS(TERT-ALKYLIMIDO)OSMIUM(VIII) AND OXOTRIS(TERT-ALKYLIMIDO)OSMIUM(VIII) COMPLEXES - STEREOSPECIFIC VICINAL DIAMINATION OF OLEFINS [J].
CHONG, AO ;
OSHIMA, K ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (10) :3420-3426
[7]   Regiodivergent Iridium(III)-Catalyzed Diamination of Alkenyl Amides with Secondary Amines: Complementary Access to γ- or δ-Lactams [J].
Conway, John H., Jr. ;
Rovis, Tomislav .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (01) :135-138
[8]   A Unified Approach to the Four Azaindoline Families by Inter-/Intramolecular Annulative Diamination of Vinylpyridines [J].
Danneman, Michael W. ;
Hong, Ki Bum ;
Johnston, Jeffrey N. .
ORGANIC LETTERS, 2015, 17 (15) :3806-3809
[9]   Cu(I)-catalyzed asymmetric diamination of conjugated dienes [J].
Du, Haifeng ;
Zhao, Baoguo ;
Yuan, Weicheng ;
Shi, Yian .
ORGANIC LETTERS, 2008, 10 (19) :4231-4234
[10]   Catalytic asymmetric allylic and homoallylic diamination of terminal olefins via formal C-H activation [J].
Du, Haifeng ;
Zhao, Baoguo ;
Shi, Yian .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (27) :8590-+