Ru3(CO)12-catalyzed C-H/CO/olefin coupling of N-pyridylindolines.: Direct carbonylation at a C-H bond δ to the pyridine nitrogen

被引：64

作者：

Chatani, N ^{[1
]}

Yorimitsu, S ^{[1
]}

Asaumi, T ^{[1
]}

Kakiuchi, F ^{[1
]}

Murai, S ^{[1
]}

机构：

[1] Osaka Univ, Dept Appl Chem, Fac Engn, Suita, Osaka 5650871, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 21期

关键词：

D O I：

10.1021/jo0259865

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of N-pyridylindolines with CO and ethylene in the presence of Ru-3(CO)(12) results in direct carbonylation at a C-H bond delta to the pyridine sp(2) nitrogen, which represents a new type of C-H/CO/olefin coupling. The presence of a pyridine ring as a directing group on the substrates is essential for the reaction to proceed. The choice of N,N-dimethylacetamide (DMA) as the solvent is crucial for the reaction to proceed efficiently.

引用

页码：7557 / 7560

页数：4

共 50 条

[21] Recent Advances in Ru-Catalyzed Olefin and C-H Bond Oxidation
Herath, Hashini N. K.
Parent, Alexander R.
CATALYSIS BY METAL COMPLEXES AND NANOMATERIALS: FUNDAMENTALS AND APPLICATIONS, 2019, 1317 : 85 - 101
[22] An Update on Oxidative C-H Carbonylation with CO
Liu, Yichang
Chen, Yi-Hung
Yi, Hong
Lei, Aiwen
ACS CATALYSIS, 2022, 12 (13) : 7470 - 7485
[23] Palladium/Copper Co-catalyzed Oxidative C-H/C-H Carbonylation of Diphenylamines: A Way To Access Acridones
Wen, Jiangwei
Tang, Shan
Zhang, Fan
Shi, Renyi
Lei, Aiwen
ORGANIC LETTERS, 2017, 19 (01) : 94 - 97
[24] Ru-3(CO)(12)-catalyzed coupling of heteroaromatic C-H/CO/olefins. Regioselective acylation of the imidazole ring
Chatani, N
Fukuyama, T
Kakiuchi, F
Murai, S
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (02) : 493 - 494
[25] Dehydrative Cp*Co(III)-Catalyzed C-H Bond Allenylation
Sen, Malay
Dahiya, Pardeep
Premkumar, J. Richard
Sundararaju, Basker
ORGANIC LETTERS, 2017, 19 (14) : 3699 - 3702
[26] Ni-Catalyzed Direct Carboxylation of an Unactivated C-H Bond with CO2
Pei, Chunzhe
Zong, Jiarui
Han, Shanglin
Li, Bin
Wang, Baiquan
ORGANIC LETTERS, 2020, 22 (17) : 6897 - 6902
[27] Rhodium-Catalyzed C-H Bond Functionalization with Amides by Double C-H/C-N Bond Activation
Meng, Guangrong
Szostak, Michal
ORGANIC LETTERS, 2016, 18 (04) : 796 - 799
[28] SYNTHESIS OF CARBAZOLE BY RU3(CO)12-CATALYZED REDUCTIVE CARBONYLATION OF 2-NITROBIPHENYL - THE CRYSTAL AND MOLECULAR-STRUCTURE OF RU3(MU-3-NC6H4-O-C6H5)2(CO)9
CROTTI, C
CENINI, S
BASSOLI, A
RINDONE, B
DEMARTIN, F
JOURNAL OF MOLECULAR CATALYSIS, 1991, 70 (02): : 175 - 187
[29] Palladium-Catalyzed Regioselective Dehydrogenative C-H/C-H Cross-Coupling of Pyrroles and Pyridine N-Oxides
Liu, Shanshan
Tzschucke, C. Christoph
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (21) : 3509 - 3513
[30] Co(iii)-catalyzed Z-selective oxidative C-H/C-H cross-coupling of alkenes with triisopropylsilylacetylene
Zhao, Tingxing
Qin, Dekun
Han, Weiguo
Yang, Shiping
Feng, Boya
Gao, Ge
You, Jingsong
CHEMICAL COMMUNICATIONS, 2019, 55 (43) : 6118 - 6121

← 1 2 3 4 5 →