84761-77-3Relevant academic research and scientific papers
A Chan-Evans-Lam approach to trisubstituted vinyl ethers
Molder, Bryce A.,Sader, Jonathan K.,Wulff, Jeremy E.
supporting information, p. 9649 - 9653 (2021/12/01)
Trisubstituted vinyl ethers were accessedviaChan-Evans-Lam coupling of vinyl trifluoroborates and primary aliphatic alcohols. This approach complements prior methods that required the use of neat liquid alcohol coupling partners. A palladium-catalyzed redox-relay Heck reaction was used to convert several vinyl ethers into aldehyde-functionalized 1,3-dihydroisobenzofurans.
Construction of spirofused tricyclic frameworks by NHC-catalyzed intramolecular stetter reaction of a benzaldehyde tether with a cyclic exsnone
Hsu, Day-Shin,Cheng, Chiao-Yun
, p. 10832 - 10842 (2019/09/30)
Various benzaldehyde tethers with a cyclic enone were prepared from commercially available 2-hydroxybenzaldehydes via a three-step sequence involving triflate formation, Sonogashira cross-coupling, and regioselective hydrogenation. These substrates were t
Carboxylate-Assisted Oxidative Addition to Aminoalkyl PdII Complexes: C(sp3)?H Arylation of Alkylamines by Distinct PdII/PdIV Pathway
Whitehurst, William G.,Blackwell, J. Henry,Hermann, Gary N.,Gaunt, Matthew J.
supporting information, p. 9054 - 9059 (2019/06/04)
Reported is the discovery of an approach to functionalize secondary alkylamines using 2-halobenzoic acids as aryl-transfer reagents. These reagents promote an unusually mild carboxylate-assisted oxidative addition to alkylamine-derived palladacycles. In the presence of AgI salts, a decarboxylative C(sp3)?C(sp2) bond reductive elimination leads to γ-aryl secondary alkylamines and renders the carboxylate motif a traceless directing group. Stoichiometric mechanistic studies were effectively translated to a Pd-catalyzed γ-C(sp3)?H arylation process for secondary alkylamines.
Catalytic Enantioselective Birch-Heck Sequence for the Synthesis of Tricyclic Structures with All-Carbon Quaternary Stereocenters
Krasley, Andrew T.,Malachowski, William P.,Terz, Hannah M.,Tran Tien, Sabrina
supporting information, p. 1740 - 1743 (2018/04/14)
A new enantioselective desymmetrizing Mizoroki-Heck reaction is reported. The process affords high yields and enantioselectivities of tricyclic structures containing all-carbon quaternary stereocenters. The substrates for the reaction are efficiently synt
Synthesis of 9,10-Diarylanthracenes via Mg(TMP) 2 ·2LiCl-Mediated Benzyne Generation/[4+2] Cycloaddition and Deoxygenation of 9,10-Epoxyanthracene Intermediates
Miyamoto, Naoya,Nakazawa, Yuki,Nakamura, Takanori,Okano, Kentaro,Sato, Sota,Sun, Zhe,Isobe, Hiroyuki,Tokuyama, Hidetoshi
supporting information, p. 513 - 518 (2017/12/08)
A new synthetic route to functionalized 9,10-diarylanthracenes has been developed. 9,10-Epoxyanthracene intermediates were prepared by [4+2] cycloaddition of 1,3-diarylisobenzofuran with a variety of functionalized benzyne intermediates, which were obtained by Mg(TMP) 2 ·2LiCl-mediated benzyne generation. For the cleavage of the resultant 9,10-epoxyanthracene intermediates, we developed mild deoxygenation conditions using a combination of trifluoroacetic acid and Et 3 SiH. The utility of this sequence was demonstrated by application to the synthesis of 5,7,12,14-tetraphenylpentacene.
Ti/Ni-mediated inter- and intramolecular conjugate addition of aryl and alkenyl halides and triflates
Marquez, Irene R.,Miguel, Delia,Millan, Alba,Marcos, M. Luisa,De Cienfuegos, Luis Alvarez,Campana, Araceli G.,Cuerva, Juan M.
, p. 1529 - 1541 (2014/03/21)
In this work, we show that the unique combination of a nickel catalyst and Cp2TiCl allows the direct conjugate addition of aryl and alkenyl iodides, bromides, and to a lesser extent, chlorides and triflates to α,β-unsaturated carbonyls at room temperature, without requiring the previous formation of an organometallic nucleophile. The reaction proceeds inter- and intramolecularly with good functional group compatibility, which is key for the development of free protecting group methodologies. Carbo- and heterocycles of five- and six-membered rings are obtained in good yields. Moreover, some insights about the mechanism involved have been obtained from cyclic voltammetry, UV-vis, and HRTEM measurements.
Pd(II)-catalyzed one-pot, three-step route for the synthesis of unsymmetrical acridines
Guo, Hai-Ming,Mao, Run-Ze,Wang, Qiao-Tian,Niu, Hong-Ying,Xie, Ming-Sheng,Qu, Gui-Rong
supporting information, p. 5460 - 5463 (2013/11/19)
Unsymmetric acridines are synthesized via a one-pot amination/cyclization/ aromatization reaction for the first time. With Pd(OAc)2-X-Phos as the catalyst, a series of unsymmetric acridines are obtained in moderate to excellent yields (up to 99
Enantioselective synthesis of multisubstituted biaryl skeleton by chiral phosphoric acid catalyzed desymmetrization/kinetic resolution sequence
Mori, Keiji,Ichikawa, Yuki,Kobayashi, Manato,Shibata, Yukihiro,Yamanaka, Masahiro,Akiyama, Takahiko
supporting information, p. 3964 - 3970 (2013/04/24)
Described herein is the enantioselective synthesis of multisubstituted biaryl derivatives by chiral phosphoric acid catalyzed asymmetric bromination. Two asymmetric reactions (desymmetrization and kinetic resolution) proceeded successively to afford chiral biaryls in excellent enantioselectivities (up to 99% ee). Both experimental and computational studies suggested that this excellent selectivity could be achieved via a highly organized hydrogen bond network among a substrate, a catalyst (chiral phosphoric acid), and a brominating reagent (N-bromophthalimide).
Cesium carbonate mediated aryl triflate esters' deprotection
Green, Alice E.,Agouridas, Vangelis,Deniau, Eric
supporting information, p. 7078 - 7079 (2013/12/04)
A variety of diversely substituted aryl triflate esters were efficiently deprotected to the parent phenols by exposure to cesium carbonate in toluene. This procedure proved highly compatible with existing functional groups.
Palladium-catalyzed desulfitative arylation by C-O bond cleavage of aryl triflates with sodium arylsulfinates
Zhou, Chao,Liu, Qingjiang,Li, Yaming,Zhang, Rong,Fu, Xinmei,Duan, Chunying
, p. 10468 - 10472 (2013/01/15)
An efficient Pd-catalyzed desulfitative coupling reaction of sodium arylsulfinates as arylation reagents by C-O bond cleavage of aryl triflates was developed. With only 2 mol % of Pd(OAc)2 as catalyst and XPhos as ligand, the reaction proceeded well for a range of substrates.
