- Dual Gold Catalysis: Synthesis of Fluorene Derivatives from Diynes
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1,5-Diyne systems bearing one terminal and one benzyl- or allyl-substituted alkyne attached to an aromatic backbone were converted in the presence of a gold catalyst. In a dual gold-catalyzed process, gold vinylidenes are formed that selectively undergo formal CH insertion into the C(sp2)–H bond of the offered unsaturated systems. If H atoms are present in the propargylic position, a subsequent isomerization to the aromatic system takes place leading to 9H-fluorene and 11H-benzo[b]fluorene derivatives as final products. In the case of a quaternary carbon in the propargylic position no further aromatization is observed and 10H-benzo[b]fluorene derivatives are obtained in high yield. (Figure presented.).
- Bucher, Janina,Wurm, Thomas,Taschinski, Svenja,Sachs, Eleni,Ascough, David,Rudolph, Matthias,Rominger, Frank,Hashmi, A. Stephen K.
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p. 225 - 233
(2017/02/05)
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- Biarylphosphonite gold(I) complexes as superior catalysts for oxidative cyclization of propynyl arenes into indan-2-ones
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Striking gold: A series of variously functionalized propynyl arenes was smoothly converted into indan-2-ones by a new gold(I)-catalyzed oxidative cyclization process. [LAu]NTf2 (Tf=trifluoromethanesulfonyl) is a superior catalyst both in terms of yield and kinetics for the present transformation. Copyright
- Henrion, Guilhem,Chavas, Thomas E. J.,Le Goff, Xavier,Gagosz, Fabien
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supporting information
p. 6277 - 6282
(2013/07/11)
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- REACTIONS OF 3-ALKYL- AND 3,3-DIALKYL-1-BROMOALLENES WITH ORGANOCUPRATES: EFFECTS OF THE NATURE OF THE CUPRATE REAGENT ON THE REGIO- AND STEREOSELECTIVITY
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Organocuprates induce 1,3- and direct substitution in 3-alkyl- and 3,3-dialkyl-1-bromo-1,2-dienes leading respectively to either terminal acetylenes or allenic hydrocarbons.The nature of the cuprate exerts a prominent role in determining both the regio- and the stereochemistry of these reactions.
- Caporusso, Anna Maria,Polizzi, Carmela,Lardicci, Luciano
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p. 6073 - 6076
(2007/10/02)
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- Synthesis of Chiral Alk-1-ynes containing an α-Phenylethyl Group
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(R)-4-Phenylpent-1-yne, (R)-(1b), and (S)-5-phenylhex-1-yne, (S)-(1c), have been synthesised from the corresponding chiral alk-1-enes (2) by a stereospecific bromination-dehydrobromination procedure.On the other hand, (R)-3-phenylbut-1-yne, (R)-(1a), has
- Caporusso, Anna Maria,Lardicci, Luciano
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p. 949 - 953
(2007/10/02)
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