38384-58-6Relevant academic research and scientific papers
1,2-Aryl Migration Induced by Amide C?N Bond-Formation: Reaction of Alkyl Aryl Ketones with Primary Amines Towards α,α-Diaryl β,γ-Unsaturated γ-Lactams
Hu, Rong,Tao, Yigao,Zhang, Xiaofeng,Su, Weiping
supporting information, p. 8425 - 8430 (2021/03/16)
Rearrangement reactions incorporated into cascade reactions play an important role in rapidly increasing molecular complexity from readily available starting materials. Reported here is a Cu-catalyzed cascade reaction of α-(hetero)aryl-substituted alkyl (hetero)aryl ketones with primary amines that incorporates an unusual 1,2-aryl migration induced by amide C?N bond formation to produce a class of structurally novel α,α-diaryl β,γ-unsaturated γ-lactams in generally good-to-excellent yields. This cascade reaction has a broad substrate scope with respect to primary amines, allows a wide spectrum of (hetero)aryl groups to smoothly undergo 1,2-migration, and tolerates electronically diverse α-substituents on the (hetero)aryl ring of the ketones. Mechanistically, this 1,2-aryl migration may stem from the intramolecular amide C?N bond formation which induces nucleophilic migration of the aryl group from the acyl carbon center to the electrophilic carbon center that is conjugated with the resulting iminium moiety.
Formal Enone α-Arylation via I(III)-Mediated Aryl Migration/Elimination
Martins, Bruna S.,Kaiser, Daniel,Bauer, Adriano,Tiefenbrunner, Irmgard,Maulide, Nuno
supporting information, p. 2094 - 2098 (2021/04/05)
A formal enone α-arylation is described. This metal-free transformation relies on the I(III)-mediated skeletal reorganization of silyl enol ethers and features mild conditions, good yields, and high stereoselectivities for β-substituted enones.
Chemoselective reduction of ?,￠-unsaturated carbonyl and carboxylic compounds by hydrogen iodide
Matsumoto, Shoji,Marumoto, Hayato,Akazome, Motohiro,Otani, Yasuhiko,Kaiho, Tatsuo
, p. 590 - 599 (2021/03/29)
The selective reduction of ?,￠-unsaturated carbonyl compounds was achieved to produce saturated carbonyl compounds with aqueous HI solution. The introduction of an aryl group at an ? or ￠ position efficiently facilitated the reduction with good yield. The reaction was applicable to compounds bearing carboxylic acids and halogen atoms. Through the investigation of the reaction mechanism, it was found that Michael-type addition of iodide occurred to produce ￠-iodo compounds followed by the reduction of C-I bond via anionic and radical paths.
Heterogeneous gold-catalyzed oxidative cross-coupling of propargylic acetates with arylboronic acids leading to (E)-α-arylenones
Liu, Dayi,Nie, Quan,Zhang, Rongli,Cai, Mingzhong
supporting information, p. 29 - 34 (2018/11/30)
An efficient heterogeneous gold-catalyzed oxidative cross-coupling of propargylic acetates with arylboronic acids has been developed that proceeds smoothly in the presence of Selectfluor and provides a general and powerful tool for the preparation of various valuable α-arylenones with moderate to good yields, excellent E-selectivity, and recyclability of the gold catalyst. The reaction is the first example of heterogeneous gold-catalyzed arylative rearrangement of propargylic acetates for construction of complex enones.
Stereodivergent Access to Enantioenriched Epoxy Alcohols with Three Stereogenic Centers via Ruthenium-Catalyzed Transfer Hydrogenation
Zhao, Zhifei,Bagdi, Prasanta Ray,Yang, Shuang,Liu, Jinggong,Xu, Weici,Fang, Xinqiang
supporting information, p. 5491 - 5494 (2019/08/01)
The resolution technique of stereodivergent reaction on racemic mixtures (stereodivergent RRM) was employed for the first time in ruthenium complex catalyzed transfer hydrogenation of racemic epoxy ketones, providing a new and very simple method that allows access to enantioenriched epoxy alcohols with three stereogenic centers in a one-step fashion. The protocol features simple reaction conditions, practical operation, ability to scale up, and broad group tolerance.
Domino Meyer-Schuster/Arylation Reaction of Alkynols or Alkynyl Hydroperoxides with Diazonium Salts Promoted by Visible Light under Dual Gold and Ruthenium Catalysis
Alcaide, Benito,Almendros, Pedro,Busto, Eduardo,Luna, Amparo
, p. 1526 - 1533 (2016/05/19)
A method for the arylative coupling of alkynols or alkynyl hydroperoxides using equimolar amounts of diazonium salts at room temperature has been achieved through application of a gold/photoredox dual catalytic system. The excess of external reagents (oxi
Copper-catalyzed arylative meyer-schuster rearrangement of propargylic alcohols to complex enones using diaryliodonium salts
Collins, Beatrice S. L.,Suero, Marcos G.,Gaunt, Matthew J.
supporting information, p. 5799 - 5802 (2013/06/27)
Free choice: A copper-catalyzed arylative Meyer-Schuster rearrangement is described. The reaction is compatible with a range of substituted propargylic alcohols and diaryliodonium salts and delivers complex trisubstituted enone products selectively as the
Synthesis of (E)-α,β-Unsaturated ketones by hydrostannylation- Stille tandem reaction of alkylarylacetylenes with acyl chlorides
Li, Jianying,Yu, Yan,Hao, Wenyan,Cai, Mingzhong
experimental part, p. 559 - 561 (2011/02/26)
(E)-α,β-Unsaturated ketones can be stereoselectively synthesised in one pot under mild conditions, in good yields, by the hydrostannylation of alkylaryl-acetylenes, followed by the Stille cross-coupling with acyl chlorides.
Iridium-Catalyzed coupling reaction of primary alcohols with 2-alkynes leading to hydroacylation products
Hatanaka, Shintaro,Obora, Yasushi,Ishii, Yasutaka
experimental part, p. 1883 - 1888 (2010/06/20)
A novel iridium-catalyzed intermolecular coupling reaction of primary alcohols or aldehydes with 2-alkynes was successfully achieved with high regioselectivity to give hydroacylation products such as α,β- unsaturated ketones in good yields. The mechanistic investigation of the reaction strongly indicated that the coupling proceeds through the initial formation of homoallylic alcohols followed by dehydrogenation to β,γ-unsatutated ketones and then isomerisation, which leads to the hydroacylation products.
Palladium-catalyzed carbonylation/acyl migratory insertion sequence
Zhang, Zhenhua,Liu, Yiyang,Gong, Mingxing,Zhao, Xiaokun,Zhang, Yan,Wang, Jianbo
scheme or table, p. 1139 - 1142 (2010/05/02)
Chemical Equation Presented On the move: A palladium-catalyzed reaction of aryl iodides, diazo compounds or N-tosylhyd razones, and carbon monoxide affords β-oxo esters or ketones/ enones (see scheme; DCE = l,2-dichloroethane). The products are delivered with high efficiency through the title sequence.
