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

[21] Cobalt-Catalyzed Tandem C-H Activation/C-C Cleavage/C-H Cyclization of Aromatic Amides with Alkylidenecyclopropanes
Li, Mingliang
Kwong, Fuk Yee
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (22) : 6512 - 6516
[22] Cobalt-Catalyzed, Chelation-Assisted C-H Bond Functionalization
Yoshikai, Naohiko
SYNLETT, 2011, (08) : 1047 - 1051
[23] Synthesis of Chiral Diarylmethylamines by Cobalt-Catalyzed Enantioselective C-H Alkoxylation
Wang, Zhen-Kai
Wu, Yong-Jie
Yao, Qi-Jun
Shi, Bing-Feng
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (28)
[24] Cobalt-Catalyzed Monoselective ortho -C-H Ethylation of Carboxamides with Triethylaluminum
Xu, Kun
Tan, Zhoumei
Zhang, Haonan
Zhang, Sheng
SYNTHESIS-STUTTGART, 2017, 49 (17): : 3931 - 3936
[25] Cobalt-Catalyzed Enantioselective C-H Carbonylation towards Chiral Isoindolinones
Teng, Ming-Ya
Wu, Yong-Jie
Chen, Jia-Hao
Huang, Fan-Rui
Liu, De-Yang
Yao, Qi-Jun
Shi, Bing-Feng
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (10)
[26] Cobalt-catalyzed C-N, C-O, C-S bond formation: synthesis of heterocycles
Kaur, Navjeet
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2019, 16 (12) : 2525 - 2553
[27] Cobalt-Catalyzed Intermolecular C-H Amidation of Unactivated Alkanes
Lee, Jeonghyo
Jin, Seongho
Kim, Dongwook
Hong, Soon Hyeok
Chang, Sukbok
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (13) : 5191 - 5200
[28] Development of Cobalt-Catalyzed C-H Bond Functionalization Reactions
Yoshikai, Naohiko
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2014, 87 (08) : 843 - 857
[29] Current Mechanistic Understanding of Cobalt-Catalyzed C-H Functionalization
Planas, Oriol
Chirila, Paula G.
Whiteoak, Christopher J.
Ribas, Xavi
ADVANCES IN ORGANOMETALLIC CHEMISTRY, VOL 69, 2018, 69 : 209 - 282
[30] Cobalt-Catalyzed Oxidative C-H Activation: Strategies and Concepts
Mei, Ruhuai
Dhawa, Uttam
Samanta, Ramesh C.
Ma, Wenbo
Wencel-Delord, Joanna
Ackermann, Lutz
CHEMSUSCHEM, 2020, 13 (13) : 3306 - 3356

← 1 2 3 4 5 →