74866-37-8Relevant articles and documents
Photoredox/cobaloxime co-catalyzed allylation of amines and sulfonyl hydrazines with olefins to access α-allylic amines and allylic sulfones
Tong, Qing-Xiao,Xu, Hui,Zhang, Hong,Zhong, Jian-Ji
, p. 8227 - 8231 (2021/10/12)
Herein, we reported a dual-catalytic platform for the allylation of amines and sulfonyl hydrazines with olefins to selectively access α-allylic amines and allylic sulfones in good yields by combining photoredox catalysis and cobaloxime catalysis. This strategy avoided the use of a stoichiometric amount of terminal oxidant and the use of pre-functionalized allylic precursors, representing a green and ideal atom- & step-economical process. Good substrate scope and gram-scale synthesis demonstrated the utility of this protocol. Mechanistic studies revealed that a radical process is probably involved in this reaction.
Ni-Catalyzed Reductive Allylation of α-Chloroboronates to Access Homoallylic Boronates
Lou, Yixian,Qiu, Jian,Yang, Kai,Zhang, Feng,Wang, Chenglan,Song, Qiuling
supporting information, p. 4564 - 4569 (2021/06/28)
The transition-metal-catalyzed allylation reaction is an efficient strategy for the construction of new carbon-carbon bonds alongside allyl or homoallylic functionalization. Herein we describe a Ni-catalyzed reductive allylation of α-chloroboronates to efficiently render the corresponding homoallylic boronates, which could be readily converted into valuable homoallylic alcohols or amines or 1,4-diboronates. This reaction features a broad substrate scope with good functional group compatibility that is complementary to the existing methods for the preparation of homoallylic boronates.
Copper-catalyzed radical oxyallylation of olefins for the construction of alkene-containing isoxazolines
He, Xiaoxue,Qian, Lijie,Dai, Yuyu,Yan, Xinhuan,Li, Xiaoqing,Xu, Xiangsheng
supporting information, (2021/05/31)
A radical-mediated approach to alkene oxyallylation using allylic oximes is described. The reaction proceeds under copper-catalytic redox-neutral conditions and tolerates various functional groups. This protocol thus enables the synthesis of structurally valuable isoxazolines and the introduction of a versatile olefin motif in a single step.
Copper-Catalyzed Intermolecular Alkynylation and Allylation of Unactivated C(sp3)-H Bonds via Hydrogen Atom Transfer
Liang, Lei,Guo, Ge,Li, Chen,Wang, Song-Lin,Wang, Yue-Hui,Guo, Hai-Ming,Niu, Hong-Ying
supporting information, p. 8575 - 8579 (2021/11/13)
We describe Cu-catalyzed intermolecular alkynylation and allylation of unactivated C(sp3)-H bonds with singly occupied molecular orbital-philes (SOMO-philes) via hydrogen atom transfer (HAT). Employing N-fluoro-sulfonamide as a HAT reagent, a set of subst
Controllable Activation of β-Alkyl Nitroalkenes: Regioselective Synthesis of Allyl and Vinyl Sulfones
Wang, Ye,Xiong, Guowei,Zhang, Chuanxin,Chen, Yunfeng
, p. 4018 - 4026 (2021/03/01)
The regiospecific radical reactions of β-alkyl nitroalkenes with sulfonyl hydrazides depended to a great extent on the choice of a solvent and catalyst. In the presence of dimethylformamide (DMF), β-alkyl nitroalkenes more likely converted into electron-rich allyl nitro compounds, which reacted with sulfonyl hydrazides to afford allyl sulfones with high regioselectivity. While in acetonitrile (CH3CN), vinyl sulfones were obtained directly via sulfonation of electron-deficient β-alkyl nitroalkenes. The mechanism investigation revealed that the regioselectivity was controlled by the equilibrium of β-alkyl nitroalkenes and allyl nitro compounds.
Silver-catalyzed decarboxylative radical allylation of α,α-difluoroarylacetic acids for the construction of CF2-allyl bonds
Wang, Pingyang,Du, Pengcheng,Sun, Qianqian,Zhang, Jianhua,Deng, Hongmei,Jiang, Haizhen
supporting information, p. 2023 - 2029 (2021/03/16)
An efficient silver-catalyzed method of decarboxylative radical allylation of α,α-difluoroarylacetic acids to build CF2-allyl bonds has been developed. Using allylsulfone as an allyl donor, α,α-difluorine substituted arylacetic acids bearing various functional groups are successfully allylated to access a series of 3-(α,α-difluorobenzyl)-1-propylene compounds in moderate to excellent yields in aqueous CH3CN solution under the mild conditions. Experimental studies disclosed that the α-fluorine substitution of arylacetic acid has a great influence on free radical activity and reactivity.
Visible-Light-Mediated Alkenylation of Alkyl Boronic Acids without an External Lewis Base as an Activator
Yue, Fuyang,Dong, Jianyang,Liu, Yuxiu,Wang, Qingmin
supporting information, p. 2477 - 2481 (2021/04/05)
Herein we report a protocol for the direct visible-light-mediated alkenylation of alkyl boronic acids at room temperature without an external Lewis base as an activator, and we propose a mechanism involving benzenesulfinate activation of the alkyl boronic acids. The protocol permits the efficient functionalization of a broad range of cyclic and acyclic primary and secondary alkyl boronic acids with various alkenyl sulfones. We demonstrated its utility by preparing or functionalizing several pharmaceuticals and natural products.
Process for the selective synthesis of allyl sulfone compounds
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Paragraph 0016-0018, (2020/11/02)
The invention relates to a method for selectively synthesizing an allylic sulfone compound. The method comprises the steps of: adding solvent to raw materials of nitroolefin and sodium sulfinate whichis stable and easy to operate, directly heating the obtained mixture while stirring is conduced, and performing treatment on the heated mixture to obtain the allylic sulfone compound. The method hasthe advantages that no addition of catalysts is needed, the whole system is open, and the yield is high; through the adoption of the direct heating method, the sodium sulfinate can be used as a mild Lewis base in the above reaction; the key step of the reaction is that the equilibrium between the nitroolefin and an allyl nitro compound is promoted by the Lewis base, and the stable nitroolefin is converted into the allyl nitro compound, which is more prone to a free-radical addition reaction, through the key step; therefore, the reaction can be conducted more easily under a mild condition, andthe speed of the reaction is increased, so that the compound with an allylic sulfone structure is effectively synthesized.
Copper-Catalyzed Decarboxylative Functionalization of Conjugated β, Γ-Unsaturated Carboxylic Acids
Zhang, Wei,Wang, Chengming,Wang, Qiu
, p. 13179 - 13185 (2020/11/17)
Copper-catalyzed decarboxylative coupling reactions of conjugated β,γ-unsaturated carboxylic acids have been achieved for allylic amination, alkylation, sulfonylation, and phosphinoylation. This approach was effective for a broad scope of amino, alkyl, su
Direct Decarboxylative Allylation and Arylation of Aliphatic Carboxylic Acids Using Flavin-Mediated Photoredox Catalysis
Ramirez, Nieves P.,Lana-Villarreal, Teresa,Gonzalez-Gomez, Jose C.
supporting information, p. 1539 - 1550 (2019/08/07)
We describe herein a direct decarboxylative allylation of aliphatic carboxylic acids with allylsulfones using visible light and riboflavin tetraacetate (RFTA) as photocatalyst. The reaction proceeds at room temperature tolerating a wide range of functiona
