Thioamide-Directed Cp*Co(III)-Catalyzed C-H Allylation of Ferrocenes

被引：25

作者：

Zhang, Zhuo-Zhuo ^{[1
]}

Liao, Gang ^{[2
]}

Chen, Hao-Ming ^{[2
]}

Shi, Bing-Feng ^{[2
,3
,4
]}

机构：

[1] Chengdu Univ, Sch Food & Biol Engn, Chengdu 610106, Sichuan, Peoples R China

[2] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China

[3] Zhengzhou Univ, Green Catalysis Ctr, Zhengzhou 450001, Peoples R China

[4] Zhengzhou Univ, Coll Chem, Zhengzhou 450001, Peoples R China

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 07期

关键词：

PLANAR CHIRAL FERROCENES; COBALT(III)-CATALYZED ALLYLATION; BOND FUNCTIONALIZATION; AMIDATION; ARYLATION; ACTIVATION; KETONES;

D O I：

10.1021/acs.orglett.1c00533

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, the first Cp*Co(III)-catalyzed C-H allylation of ferrocene thioamides with allyl carbonates has been developed. This reaction is compatible with a wide range of functional groups, providing various allylated ferrocene derivatives in up to 90% yields. In addition, the C-H allylation protocol is also compatible with the use of vinylcyclopropanes as allylating reagents by merging C-H and C-C activation into one catalytic system. Mechanistic studies revealed that the thiocarbonyl-directing group plays a vital role in C-H activation.

引用

页码：2626 / 2631

页数：6

共 50 条

[41] Cp*Co(III)-Catalyzed C-H Acylmethylation of Arenes by Employing Sulfoxonium Ylides as Carbene Precursors
Ji, Shuying
Yan, Kelu
Li, Bin
Wang, Baiquan
ORGANIC LETTERS, 2018, 20 (18) : 5981 - 5984
[42] Ir(iii)-catalyzed thioether directed arene C-H alkenylation
Li, Chen
Chen, Xian
Bao, Rui-Peng
Li, Dong-Li
Zhang, Kun
Wang, Dong-Hui
RSC ADVANCES, 2019, 9 (52) : 30134 - 30138
[43] Mechanistic exploration of Rh(III)-catalyzed C-H allylation of benzamides with allyl bromide
Pal, Poulami
Mondal, Sonjoy
Chatterjee, Arpita
Saha, Rohini
Chakrabarty, Kuheli
Das, GourabKanti
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2021, 949
[44] Indazolones Directed Rh(III)-Catalyzed C-H Amidation of Arenes
Chen, Shao-Yong
Zheng, Yi-Chuan
Liu, Xu-Ge
Song, Jia-Lin
Shu, Bing
Zheng, Tao
Xiao, Lin
Zhang, Shang-Shi
Cao, Hua
ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (18) : 3302 - 3309
[45] Access to Sultams by Rhodium(III)-Catalyzed Directed C-H Activation
Pham, Manh V.
Ye, Baihua
Cramer, Nicolai
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (42) : 10610 - 10614
[46] Manganese(I)-Catalyzed Substitutive C-H Allylation
Liu, Weiping
Richter, Sven C.
Zhang, Yujiao
Ackermann, Lutz
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (27) : 7747 - 7750
[47] Thioketone-Directed Palladium(II)-Catalyzed C-H Arylation of Ferrocenes with Aryl Boronic Acids
Cai, Zhong-Jian
Liu, Chen-Xu
Gu, Qing
You, Shu-Li
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (05) : 1296 - 1299
[48] Rhodium(III)-catalyzed C-H/C-C activation sequence: vinylcyclopropanes as versatile synthons in direct C-H allylation reactions
Wu, Jia-Qiang
Qiu, Zhi-Ping
Zhang, Shang-Shi
Liu, Jing-Gong
Lao, Ye-Xing
Gu, Lian-Quan
Huang, Zhi-Shu
Li, Juan
Wang, Honggen
CHEMICAL COMMUNICATIONS, 2015, 51 (01) : 77 - 80
[49] Inherent directing group-enabled Co(<sc>iii</sc>)-catalyzed C-H allylation/vinylation of isoquinolones
Sachin
Sharma, Tamanna
Chandra, Devesh
Sumit
Sharma, Upendra
CHEMICAL COMMUNICATIONS, 2024, 60 (43) : 5626 - 5629
[50] Recent Development on Cp*Ir(III)-Catalyzed C-H Bond Functionalization
Li, Xianwei
Ouyang, Wensen
Nie, Jianhong
Ji, Shaomin
Chen, Qian
Huo, Yanping
CHEMCATCHEM, 2020, 12 (09) : 2358 - 2384

← 1 2 3 4 5 →