Cobalt-Catalyzed Electrophilic Amination of Aryl- and Heteroarylzinc Pivalates with N-Hydroxylamine Benzoates

被引：70

作者：

Chen, Yi-Hung ^{[1
]}

Grassl, Simon ^{[1
]}

Knochel, Paul ^{[1
]}

机构：

[1] Ludwig Maximilians Univ Munchen, Dept Chem, Butenandtstr 5-13, D-81377 Munich, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 04期

关键词：

cobalt catalysis; cross-coupling; electrophilic amination; organozinc pivalates; tuberculosis; CARBON-NITROGEN BONDS; CENTER-DOT-LICL; SENSITIVE AROMATICS; ZINC REAGENTS; ENHANCED AIR; COPPER; PALLADIUM; ARENES; HETEROARENES; NUCLEOPHILES;

D O I：

10.1002/anie.201710931

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Aryl- and heteroarylzinc pivalates can be aminated with O-benzoylhydroxylamines at 25 degrees C within 2-4 h in the presence of 2.5-5.0% CoCl2 center dot 2LiCl to furnish the corresponding tertiary arylated or heteroarylated amines in good yields. This electrophilic amination also provides access to diarylamines and aryl(heteroaryl)amines. A new tuberculosis drug candidate (Q203) was prepared in six steps and 56% overall yield by using this cobalt-catalyzed amination as the key step.

引用

页码：1108 / 1111

页数：4

共 79 条

[1] Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures [J].

AbdelMagid, AF ;

Carson, KG ;

Harris, BD ;

Maryanoff, CA ;

Shah, RD .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) :3849-3862

[2]

[Anonymous], 2012, Angew. Chem. Int. Ed.

[3]

[Anonymous], 2014, ANGEW CHEM-GER EDIT

[4] Developments in Transition-Metal-Catalyzed Reactions Using Electrophilic Nitrogen Sources [J].

Barker, Timothy J. ;

Jarvo, Elizabeth R. .

SYNTHESIS-STUTTGART, 2011, (24) :3954-3964

[5] The Complementary Competitors: Palladium and Copper in C-N Cross-Coupling Reactions [J].

Beletskaya, Irina P. ;

Cheprakov, Andrei V. .

ORGANOMETALLICS, 2012, 31 (22) :7753-7808

[6] Copper-catalyzed electrophilic amination of organozinc nucleophiles:: Documentation of O-benzoyl hydroxylamines as broadly useful R2N(+) and RHN(+) synthons [J].

Berman, AM ;

Johnson, JS .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (01) :219-224

[7] Copper-catalyzed electrophilic amination of functionalized diarylzinc reagents [J].

Berman, AM ;

Johnson, JS .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (01) :364-366

[8] Copper-catalyzed electrophilic amination of diorganozinc reagents [J].

Berman, AM ;

Johnson, JS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (18) :5680-5681

[9]

Bernhardt S., 2011, ANGEW CHEM, V123, P9372

[10] Preparation of Solid Salt-Stabilized Functionalized Organozinc Compounds and their Application to Cross-Coupling and Carbonyl Addition Reactions [J].

Bernhardt, Sebastian ;

Manolikakes, Georg ;

Kunz, Thomas ;

Knochel, Paul .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (39) :9205-9209

← 1 2 3 4 5 6 7 8 →