82320-69-2Relevant academic research and scientific papers
Fe-Catalyzed Cycloisomerization of Aryl Allenyl Ketones: Access to 3-Arylidene-indan-1-ones
Teske, Johannes,Plietker, Bernd
supporting information, p. 2257 - 2260 (2018/04/27)
A cycloisomerization of aryl allenyl ketones to 3-arylidene-indan-1-ones using a cationic Fe-complex as a catalyst is reported. The catalyst opens a synthetically interesting reaction pathway to this surprisingly underrepresented class of indanones that are not accessible using alternative catalytic systems.
New gas-phase domino processes leading to benzopyranones and benzofurans
Aitken, R. Alan,Chang, Da
, p. 164 - 184 (2017/03/11)
A new domino approach to flavones by gas phase pyrolysis of β,γ-dioxophosphonium ylides containing a 2-methoxyphenyl group is frustrated by unexpected and novel decarbonylation of the intermediate flavon-3-yl radical leading to 2-phenylbenzofuran. Alternative approaches based on dioxolane protection of one carbonyl, or selective elimination in β,β′-dioxo or β-oxo-β′-thioxo ylides were not successful, but pyrolysis of a β-oxo-β′-phenylimino ylide did give the required domino reaction leading to a protected benzopyranone in moderate yield.
Highly efficient route to functionalized tetrahydrocarbazoles using a tandem cross-metathesis/intramolecular-hydroarylation sequence
An, Xiao-Lei,Chen, Jia-Rong,Li, Chang-Feng,Zhang, Fu-Gen,Zou, You-Quan,Guo, Ying-Cen,Xiao, Wen-Jing
supporting information; experimental part, p. 2258 - 2265 (2011/06/11)
The scope of the novel ruthenium-catalyzed tandem cross-metathesis/ intramolecular-hydroarylation sequence is described. This methodology offers a practical and efficient synthesis of structurally diverse and complex tetrahydrocarbazoles in good to excellent yields (up to 98%). Moreover, preliminary efforts towards the development of an enantioselective version of the current process by sequential catalysis with ruthenium complex and chiral amine are presented, with high yields and enantioselectivities (up to 88% yield and 91% ee).
SHOP-type nickel complexes with alkyl substituents on phosphorus, synthesis and catalytic ethylene oligomerization
Kermagoret, Anthony,Braunstein, Pierre
, p. 822 - 831 (2008/09/20)
The β-keto phosphorus ylides (n-Bu)3P=CHC(O)Ph 6, (t-Bu)2PhP=CHC(O)Ph 7, (t-Bu)Ph2P=CHC(O)Ph 8, (n-Bu) 2PhP=CHC(O)Ph 9, (n-Bu)Ph2P=CHC(O)Ph 10, Me 2PhP=CHC(O)Ph 11 and Ph3P=CHC(O)(o-OMe-C6H 4) 12 have been synthesized in 80-96% yields. The Ni(ii) complexes [N=iPh{Ph2PCHC(O=)(o-OMeC6H4)}(PPh 3)] 13, [N=iPh{Ph(t-Bu)PCHC(O=)Ph}(PPh3)] 15, [N=iPh{(n-Bu)2PCHC(O=)Ph}(PPh3)] 16 and [N=iPh{Ph(n-Bu)PCHC(O=)Ph}(PPh3)] 17 have been prepared by reaction of equimolar amounts of [Ni(COD)2] and PPh3 with the β-keto phosphorus ylides 12 or 8-10, respectively, and characterized by 1H and 31P{1H} NMR spectroscopy. NMR studies and the crystal structure determination of 13 indicated an interaction between the hydrogen atom of the C-H group α to phosphorus and the ether function. The complexes [N=iPh{Ph2PCHC(O=)Ph}(Py)] 18, [N=iPh{Ph(t-Bu)PCHC(O=) Ph}(Py)] 19, [N=iPh{(n-Bu)2PCHC(O=)Ph}(Py)] 20, [N=iPh{Ph(n-Bu) PCHC(O=)Ph}(Py)] 21 and [N=iPh{Me2PCHC(O=)Ph}(Py)] 22 have been isolated from the reactions of [Ni(COD)2] and an excess of pyridine with the β-keto phosphorus ylides Ph3PCH=C(O)Ph 3 or 8-11, respectively, and characterized by 1H and 31P{ 1H} NMR spectroscopy. Ligands 3, 8, 10 and 12 have been used to prepare in situ oligomerization catalysts by reaction with one equiv. of [Ni(COD)2] and PPh3 under an ethylene pressure of 30 or 60 bar. The catalyst prepared in situ from 12, [Ni(COD)2] and PPh 3 was the most active of the series with a TON of 12 700 mol C 2H4 (mol Ni)-1 under 30 bar ethylene. When the β-keto phosphorus ylide 8 was reacted in situ with three equiv. of [Ni(COD)2] and one equiv. of PPh3 under 30 bar of ethylene, ethylene polymerization was observed with a TON of 5500 mol C 2H4 (mol Ni)-1. The Royal Society of Chemistry.
