36707-30-9Relevant academic research and scientific papers
Rhodium-Catalyzed Regiodivergent Synthesis of Alkylboronates via Deoxygenative Hydroboration of Aryl Ketones: Mechanism and Origin of Selectivities
Zhang, Bing,Xu, Xin,Tao, Lei,Lin, Zhenyang,Zhao, Wanxiang
, p. 9495 - 9505 (2021/08/04)
Here, we report an efficient rhodium-catalyzed deoxygenative borylation of ketones to synthesize alkylboronates, in which the regioselectivity can be switched by the choice of the ligand. The linear alkylboronates were obtained exclusively in the presence of P(nBu)3, and PPh2Me favored the formation of branched alkylboronates. The protocol also allows access to 1,1,2-triboronates from the readily available ketones. Mechanistic studies suggest that this Rh-catalyzed deoxygenative borylation of ketones goes through an alkene intermediate, which undergoes regiodivergent hydroboration to afford linear and branched alkylboronates. The different steric effects of PPh2Me and P(nBu)3 were found to be responsible for product selectivity by density functional theory calculations. The alkene intermediate can alternatively undergo sequential dehydrogenative borylation and hydroboration to deliver the triboronates.
Harnessing Alkyl Amines as Electrophiles for Nickel-Catalyzed Cross Couplings via C-N Bond Activation
Basch, Corey H.,Liao, Jennie,Xu, Jianyu,Piane, Jacob J.,Watson, Mary P.
, p. 5313 - 5316 (2017/04/27)
We developed a strategy to harness alkyl amines as alkylating agents via C-N bond activation. This Suzuki-Miyaura cross coupling of alkylpyridinium salts, readily formed from primary amines, is the first example of a metal-catalyzed cross coupling via C-N bond activation of an amine with an unactivated alkyl group. This reaction enjoys broad scope and functional group tolerance. Primary and secondary alkyl groups can be installed. Preliminary studies suggest a NiI/NiIII catalytic cycle.
Synthesis of Two Natural Furan-Cyclized Diarylheptanoids via 2-Furaldehyde
Se?inti, Hatice,Se?en, Hasan
, p. 938 - 944 (2015/11/23)
Two natural diarylheptanoids, 2-benzyl-5-(2-phenylethyl)furan (1) and 2-methoxy-4-{[5-(2-phenylethyl)furan-2-yl]methyl}phenol (2), were synthesized starting from 2-furaldehyde. A Wittig reaction of 2-furaldehyde with benzyltriphenylphosphonium bromide followed by reduction of the alkene C=C bond with Mg gave 2-(2-phenylethyl)furan (5). Lithiation of 5 with BuLi at -78 followed by alkylation with benzyl bromide gave natural product 1. In another approach, Friedel-Crafts acylation of compound 5 with benzoyl chloride followed by deoxygenation of the C=O group afforded 1. The natural product 2 was also synthesized by acylation of 5 with 4-acetoxy-3-methoxybenzoyl chloride (16) followed by deoxygenation and deacetylation.
One-pot synthesis of 1-azaspiro frameworks initiated by photooxidation of simple furans
Kalaitzakis, Dimitris,Antonatou, Eirini,Vassilikogiannakis, Georgios
supporting information, p. 400 - 402 (2014/01/06)
A range of 1-azaspirocycles, spiroaminals and 1,6-diazaspirocycles has been synthesized, starting from simple and readily accessible furan precursors, using a cascade reaction sequence initiated by singlet oxygen.
Palladium-catalyzed reactions of enol ethers: Access to enals, furans, and dihydrofurans
Lauer, Matthew G.,Henderson, William H.,Awad, Amneh,Stambuli, James P.
, p. 6000 - 6003 (2013/02/25)
The palladium-catalyzed oxidation of alkyl enol ethers to enals, which employs low loadings of a palladium catalyst, is described. The mild oxidation conditions tolerate a diverse array of functional groups, while allowing the formation of di-, tri-, and tetrasubtituted olefins. The application of this methodology to intramolecular reactions of alkyl enol ethers containing pendant alcohols provides furan and 2,5-dihydrofuran products.
Ru- and Pd-catalysed synthesis of 2-arylfurans by one-flask heck arylation/oxidation
Schmidt, Bernd,Geissler, Diana
supporting information; experimental part, p. 4814 - 4822 (2011/10/09)
2,5-Disubstituted furans were synthesized by one-flask Heck arylation/oxidation sequences. The starting materials are 2-substituted 2,3-dihydrofurans, conveniently available by RCM/isomerization sequences, and arenediazonium salts. These react in ligand-free Heck reactions to afford 2,5-disubstituted 2,5-dihydrofurans, which are oxidized to the corresponding furans without isolation or intermediate workup. The oxidation is conveniently achieved with chloranil or DDQ, depending on the substrate.
Efficient one-pot synthesis of 2-substituted furans from 3,3-diethoxypropyne and aldehydes using a Ti(O-i-Pr)4/2i-PrMgCl reagent
Eom, Deok Ki,Choi, Seong Jib,An, Duk Keun
, p. 1141 - 1146 (2008/02/08)
A new, efficient and direct synthetic method for synthesizing 2-substituted furans using titanium-alkyne complex from easily preparable lithium propargyl alcohol derivatives derived from commercially available 3,3-diethoxypropyne, n-butyllithium and aldehydes by a Ti(O-i-Pr)4/2 i-PrMgCl reagent in 68-85percent yields.
Preparation of furans by palladium-catalyzed reaction of acylchromates and propargylic tosylates
Nakamura, Masaki,Yamane, Motoki,Sakurai, Hidehiro,Narasaka, Koichi
, p. 333 - 345 (2007/10/03)
Substituted furans are prepared by the palladium-catalyzed reaction of propargylic tosylates with acylchromates. The reaction is initiated by the oxidative additiion of propagylic tosylates to palladium(O) complexes to give 1,2-propadienylpalladium(II) co
A Convenient Method for the Preparation of Furan and Pyrrole Derivatives via Palladium(II)-Catalyzed Intramolecular Cyclization of 3- and 4-Alkenyl Alcohol or Amine Derivatives
Igarashi, Susumu,Haruta, Yoshihisa,Ozawa, Motoyasu,Nishide, Yoshiyuki,Kinoshita, Hideki,Inomata, Katsuhiko
, p. 737 - 740 (2007/10/02)
Several furan and pyrrole derivatives were prepared through palladium(II)-catalyzed intramolecular cyclization of 2-(p-toluenesulfonyl)-3-butenols and 2-methanesulfonyl-4-pentenyl alcohol or amine derivatives in good yields.
Preparation des acides alkyl et arylalkyl-5 methyl-2 benzofurannedicarboxyliques-6,7. Application a la synthese de derives de nouveaux heterocycles
Cabares, Jacques,Mavoungou-Gomes, Louis
, p. 401 - 412 (2007/10/02)
Direct formation of 5-alkyl or arylalkyl 2-methylbenzofuran 6,7-dicarboxylic acid derivatives from Diels-Alder adducts of 5-alkyl or arylalkyl 2-acetonylfurans and dimethyl acetylenedicarboxylate is promoted by boron trifluoride etherate in methylene chloride at room temperature.The structures of these new compounds were established from their 1H and 13C nmr spectra.In 1,1,2,2-tetrachloroethane and in the presence of aluminium chloride, 5-arylalkylbenzofuran anhydrides undergo an intramolecular Friedel-Crafts acylations leading to new polycyclic benzofuran derivatives.
