31600-86-9Relevant articles and documents
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Roberts,Curtin
, p. 1658 (1946)
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Asymmetric synthesis of metallocenes through enantioselective addition of organolithium reagents to 6-(dimethylamino)fulvene
Suzuka, Toshimasa,Ogasawara, Masamichi,Hayashi, Tamio
, p. 3355 - 3359 (2002)
Enantioselective addition of aryllithiums 2a-d (Ar = Ph (a), 2-MeC6H4 (b), 2-MeOC6H4 (c), 1-naphthyl (d)) to 6-(dimethylamino)fulvene (1) in the presence of (-)-sparteine in toluene at -78°C generated chiral cyclopentadienyllithiums (4) substituted with an N,N-dimethylamino(aryl)methyl group, where the enantioselectivities are 51, 91, 90, and 83% for 4a, 4b, 4c, and 4d, respectively. Treatment of the chiral cyclopentadienides 4 with FeCl2 or Fe(acac)2 gave ferrocenes, which contain an N,N-dimethylamino(aryl)methyl side chain on both of the cyclopentadienyl rings. The enantiomeric purity of the chiral ferrocenes 7 thus obtained is 99% ee or higher for those containing a 2-MeC6H4 (7b) or a 2-MeOC6H4 (7c) group.
Ortholithiation of anisole by n-BuLi-TMEDA: Reaction via disolvated dimers
Rennels,Maliakal,Collum
, p. 421 - 422 (1998)
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Reductive Elimination from Phosphine-Ligated Alkylpalladium(II) Amido Complexes to Form sp3 Carbon-Nitrogen Bonds
Peacock, D. Matthew,Jiang, Quan,Hanley, Patrick S.,Cundari, Thomas R.,Hartwig, John F.
supporting information, p. 4893 - 4904 (2018/04/16)
We report the formation of phosphine-ligated alkylpalladium(II) amido complexes that undergo reductive elimination to form alkyl-nitrogen bonds and a combined experimental and computational investigation of the factors controlling the rates of these react
Palladium-Catalyzed, Site-Selective Direct Allylation of Aryl C-H Bonds by Silver-Mediated C-H Activation: A Synthetic and Mechanistic Investigation
Lee, Sarah Yunmi,Hartwig, John F.
supporting information, p. 15278 - 15284 (2016/12/06)
We describe a method for the site-selective construction of a C(aryl)-C(sp3) bond by the palladium-catalyzed direct allylation of arenes with allylic pivalates in the presence of AgOPiv to afford the linear (E)-allylated arene with excellent regioselectivity; this reaction occurs with arenes that have not undergone site-selective and stereoselective direct allylation previously, such as monofluorobenzenes and non-fluorinated arenes. Mechanistic studies indicate that AgOPiv ligated by a phosphine reacts with the arene to form an arylsilver(I) species, presumably through a concerted metalation-deprotonation pathway. The activated aryl moiety is then transferred to an allylpalladium(II) intermediate formed by oxidative addition of the allylic pivalate to the Pd(0) complex. Subsequent reductive elimination furnishes the allyl-aryl coupled product. The aforementioned proposed intermediates, including an arylsilver complex, have been isolated, structurally characterized, and determined to be chemically and kinetically competent to undergo the proposed elementary steps of the catalytic cycle.