Unexpected C-C Bond Formation with a Ferrocenyl Fischer Carbene Complex

被引：1

作者：

Veit, Philipp ^{[1
]}

Seibert, Sebastian ^{[1
]}

Foerster, Christoph ^{[1
]}

Heinze, Katja ^{[1
]}

机构：

[1] Johannes Gutenberg Univ Mainz, Dept Chem, Duesbergweg 10-14, D-55128 Mainz, Germany

来源：

ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE | 2020年 / 646卷 / 13期

关键词：

Carbene complexes; Chromium; C-C coupling; Cyclobutenone; Ferrocene; DOTZ REACTION; BASIS-SETS; CHEMICAL MULTITALENTS; NUCLEOPHILE ADDITION; CHROMIUM; ALKYNES; CYCLOBUTENONES; INSERTION; TUNGSTEN; LIGANDS;

D O I：

10.1002/zaac.201900350

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Thermolysis of (OC)(5)Cr(C(OEt)(Fc)) (1) gives 2,N-diferrocenyl acetamide Fc-CH2-CO-NH-Fc (2) in the presence of amino ferrocene Fc-NH2. In the absence of a nucleophile, 4-ethoxy-2,3,4-triferrocenyl-cyclobut-2-enone (3) forms from 1 under thermal activation. Single crystal X-ray diffraction, NMR spectroscopy and mass spectrometry unambiguously confirm the structure of both unexpected products. Quantum chemical calculations and kinetic experiments by mass spectrometry and IR spectroscopy help to propose conceivable pathways to their formation.

引用

页码：940 / 947

页数：8

共 50 条

[21] Industrial enzymatic C-C bond formation
Mink, Daniel
Schurmann, Martin
Jennewein, Stefan
Wolberg, Michael
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
[22] C-C Bond Formation in Diiron Complexes
Mazzoni, Rita
Salmi, Mauro
Zanotti, Valerio
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (33) : 10174 - 10194
[23] Immobilization of Aldolase for C-C Bond Formation
Aragon, Caio C.
Palomo, Jose M.
Filice, Marco
Mateo, Cesar
CURRENT ORGANIC CHEMISTRY, 2016, 20 (11) : 1243 - 1251
[24] An ELF analysis of the C-C bond formation step in the N-heterocyclic carbene-catalyzed hydroacylation of unactivated C-C double bonds
Domingo, Luis R.
Saez, Jose A.
Arno, Manuel
RSC ADVANCES, 2012, 2 (18) : 7127 - 7134
[25] Unexpected C-C bond cleavage of -nitroketone in the presence of TsNBr2: A new pathway for C-N bond formation
Sarma, Manas Jyoti
Phukan, Prodeep
SYNTHETIC COMMUNICATIONS, 2016, 46 (03) : 257 - 262
[26] Photochemistry of 2-indolyl aryl ethers: An unexpected rearrangement leading to C-C bond formation
Feldman, KS
Vidulova, DB
HETEROCYCLES, 2003, 60 (07) : 1615 - 1623
[27] Application of a Bis(silylene) Nickel Complex as Precatalyst in C-C Bond Formation Reactions
Someya, Chika I.
Haberberger, Michael
Wang, Wenyuan
Enthaler, Stephan
Inoue, Shigeyoshi
CHEMISTRY LETTERS, 2013, 42 (03) : 286 - 288
[28] Cytochrome C oxidase active site mimics:: New ligands for copper and an unexpected oxidative C-C bond formation
Landaverry, Yakira R.
White, Lumberly N.
Olmstead, Marilyn M.
Einarsdottir, Olof
Konopelski, Joseph P.
HETEROCYCLES, 2006, 70 : 147 - +
[29] New methods for enantioselective C-C bond formation
Corey, EJ
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 225 : U359 - U359
[30] ZR MEDIATED C-C BOND FORMATION CHEMISTRY
JORDAN, RF
GUO, ZY
GURAM, AS
RODEWALD, S
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1993, 205 : 38 - INOR

← 1 2 3 4 5 →