Triazolylidene Ligands Allow Cobalt-Catalyzed C-H/C-O Alkenylations at Ambient Temperature

被引：13

作者：

Sauermann, Nicolas ^{[1
]}

Loup, Joachim ^{[1
]}

Kootz, Darius ^{[2
]}

Yatham, V. Reddy ^{[2
]}

Berkessel, Albrecht ^{[2
]}

Ackermann, Lutz ^{[1
]}

机构：

[1] Georg August Univ, Inst Organ & Biomol Chem, Tammannstr 2, D-37077 Gottingen, Germany

[2] Univ Cologne, Organ Chem, Dept Chem, Greinstr 4, D-50939 Cologne, Germany

来源：

SYNTHESIS-STUTTGART | 2017年 / 49卷 / 15期

关键词：

carbene; cobalt; C-H activation; C-O functionalization; triazolylidene; H BOND ACTIVATION; CROSS-COUPLING REACTIONS; SECONDARY ALKYL-HALIDES; SELECTIVE FUNCTIONALIZATION; OLEFIN METATHESIS; AROMATIC IMINES; STABLE CARBENE; ARYLATIONS; COMPLEXES; PHOSPHATES;

D O I：

10.1055/s-0036-1590471

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Direct alkenylation through C-H/C-O cleavage was accomplished under mild reaction conditions by cobalt catalysts derived from novel triazolylidene ligands. The most effective ligand is characterized by sterically demanding substituents on the 1,4-N-atoms of the triazolylidene neighboring the carbene center. The C-H alkenylations proved viable with alkenyl acetates, carbamates, carbonates and phosphates. For acyclic electrophiles, diastereoconvergent C-O functionalizations were observed.

引用

页码：3476 / 3484

页数：9

共 50 条

[31] Enantio- and Regioselective Electrooxidative Cobalt-Catalyzed C-H/N-H Annulation with Alkenes
Yao, Qi-Jun
Huang, Fan-Rui
Chen, Jia-Hao
Zhong, Ming-Yu
Shi, Bing-feng
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (11)
[32] Cobalt-Catalyzed C-H Thiolation through Dehydrogenative Cross-Coupling
Gensch, Tobias
Klauck, Felix J. R.
Glorius, Frank
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (37) : 11287 - 11291
[33] Cobalt-Catalyzed C-H Arylations, Benzylations, and Alkylations with Organic Electrophiles and Beyond
Ackermann, Lutz
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (19) : 8948 - 8954
[34] Cobalt-Catalyzed C-H Alkoxylation of Ferrocenes with Alcohols under Mild Conditions
Zhang, Zhuo-Zhuo
Cheng, Jie
Yao, Qi-Jun
Yue, Qiang
Zhou, Gang
ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (16) : 3946 - 3951
[35] Cobalt-Catalyzed C-H Benzylation of 8-Aminoquinolines on C(5) Position
Zhang, Jiaheng
Hao, Xinqi
Wang, Zhenglong
Ren, Changjiu
Niu, Junlong
Song, Maoping
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2017, 37 (05) : 1237 - 1245
[36] Construction of Planar Chiral Ferrocenes by Cobalt-Catalyzed Enantioselective C-H Acyloxylation Enabled by Dual Ligands
Huang, Fan-Rui
Zhang, Peng
Yao, Qi-Jun
Shi, Bing-Feng
CCS CHEMISTRY, 2023, 6 (11): : 2783 - 2793
[37] Mechanochemical Cobalt-Catalyzed C-H Bond Functionalizations by Ball Milling
Cheng, Hanchao
Hernandez, Jose G.
Bolm, Carsten
ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (09) : 1800 - 1804
[38] Cobalt-Catalyzed Enantioselective Directed C-H Alkylation of Indole with Styrenes
Lee, Pin-Sheng
Yoshikai, Naohiko
ORGANIC LETTERS, 2015, 17 (01) : 22 - 25
[39] Allenes: Versatile Building Blocks in Cobalt-Catalyzed C-H Activation
Shukla, Rahul K.
Nair, Akshay M.
Volla, Chandra M. R.
SYNLETT, 2021, 32 (12) : 1169 - 1178
[40] Cobalt-catalyzed C-H activation and isocyanide insertion of tryptamine derivatives
Zhu, Yiwen
Wang, Jing
Ying, Jun
Wu, Xiao-Feng
TETRAHEDRON, 2023, 143

← 1 2 3 4 5 →