Preparation of Vinylphosphonates from Ketones Promoted by Tf2O DOI
Nana Xin,

Yong-Zheng Lv,

Yongjian Lian

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(5), P. 2898 - 2907

Published: Feb. 21, 2023

An efficient triflic anhydride promoted phosphorylation of ketone was disclosed, and vinylphosphorus compounds were prepared under solvent- metal-free conditions. Both aryl alkyl ketones could perform smoothly to give vinyl phosphonates in high excellent yields. In addition, the reaction easy carry out scale up. Mechanistic studies suggested that this transformation might involve nucleophilic vinylic substitution or a addition–elimination mechanism.

Language: Английский

Recent Advances in Reactions Using Enaminone in Water or Aqueous Medium DOI

Zhouying Wang,

Baoli Zhao,

Yunyun Liu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(9), P. 1508 - 1521

Published: April 8, 2022

Abstract Enaminones have in the past decade received renewed interest organic synthesis by acting as highly versatile building blocks. Particularly, featured amino and carbonyl group enaminone structure endow them with ability of tolerating water via hydrogen bonding effect. Thus, designing synthetic methods aqueous medium enaminones main blocks has extensive attention notable success. Based on our longstanding efforts interests chemistry, we review herein research advances participated medium. magnified image

Language: Английский

Citations

83

Recent advances in transition metal-free annulation toward heterocycle diversity based on the C–N bond cleavage of enaminone platform DOI
Xiao Yun Chen, Xiaotong Zhang, Jie‐Ping Wan

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(12), P. 2356 - 2369

Published: Jan. 1, 2022

Enaminones and analogous stable enamines are well known as platform building blocks in organic synthesis for the construction of heterocyclic compounds, especially N-heterocycles. To date, enaminones have been successfully employed various 5- or 6- membered heterocycles. Recently, synthetic protocols accomplished by diversity-oriented annulation reactions based on C-N bond cleavage gained notable success. In this review, development transition metal-free product featuring a is reviewed.

Language: Английский

Citations

78

Recent advances in visible light-mediated chemical transformations of enaminones DOI
Yu Han,

Liyun Zhou,

Chengyu Wang

et al.

Chinese Chemical Letters, Journal Year: 2023, Volume and Issue: 35(2), P. 108977 - 108977

Published: Aug. 26, 2023

Language: Английский

Citations

63

Copper-catalyzed C–H/N–H annulation of enaminones and alkynyl esters for densely substituted pyrrole synthesis DOI
Leiqing Fu, Jie‐Ping Wan,

Liyun Zhou

et al.

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(11), P. 1808 - 1811

Published: Jan. 1, 2022

Herein, the copper-catalyzed annulation of enaminones with alkynyl esters for facile synthesis different pyrroles a 2,3,4,5-tetrasubstituted structure has been developed. With Cu(OAc)2 as only catalyst, tunable 2-vinyl and 2,3-dicarboxyl-functionalized achieved by using terminal internal esters, respectively. The represents first example accessing substituted via direct cascade reactions involving vinylation pyrrole ring formation.

Language: Английский

Citations

42

“Alkene-to-Alkene” Difunctionalization of Enaminones for the Synthesis of Polyfunctionalized Alkenes by Transition-Metal-Free C–H and C–N Bond Transformation DOI

J. Ye,

Yunyun Liu,

Jin Luo

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(47), P. 8451 - 8456

Published: Nov. 16, 2023

The three-component reactions of enaminones, disulfides, and alcohols for the synthesis polyfunctionalized alkenes have been realized via C-H C-N bond transformation on enaminones. proceed in a novel "alkene-to-alkene" difunctionalization mode without using any transition metal. application alkene products divergent sulfenyl heteroaryls, including sulfenylated pyrazoles, pyrimidines, isoxazoles, simple annulation has also verified.

Language: Английский

Citations

29

Recent advances in transition metal-catalyzed transformations in N,N-disubstituted enaminones DOI
Leiqing Fu, Jie‐Ping Wan

Tetrahedron Letters, Journal Year: 2023, Volume and Issue: 130, P. 154766 - 154766

Published: Sept. 26, 2023

Language: Английский

Citations

28

Three-Component Fusion to Pyrazolo[5,1-a]isoquinolines via Rh-Catalyzed Multiple Order Transformation of Enaminones DOI

Demao Chen,

Changfeng Wan, Yunyun Liu

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(7), P. 4833 - 4838

Published: March 22, 2023

A facile and practical method for the synthesis of fused tricyclic pyrazolo[5,1-a]isoquinolines has been realized via reactions enaminones, hydrazine hydrochloride, internal alkynes. By means Rh catalysis, extraordinary high-order bond functionalization, including transformation aryl C–H, ketone C═O, alkenyl C–N bonds in marks major feature cascade reactions. The results disclose individual advantage enaminones design novel efficient synthetic methods.

Language: Английский

Citations

23

I2-DMSO mediated tetra-functionalization of enaminones for the construction of novel furo[2′,3′:4,5]pyrimido[1,2-b]indazole skeletons via in situ capture of ketenimine cations DOI
You Zhou, Li‐Sheng Wang,

Shuang‐Gui Lei

et al.

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: 36(1), P. 109799 - 109799

Published: March 20, 2024

Language: Английский

Citations

10

Ultrasound-Promoted Synthesis of α-Thiocyanoketones via Enaminone C═C Bond Cleavage and Tunable One-Pot Access to 4-Aryl-2-aminothiazoles DOI
Yunyun Liu, Tao Zhang, Jie‐Ping Wan

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(12), P. 8248 - 8255

Published: May 26, 2022

Ultrasound has been successfully employed to promote the thiocyanation of C═C bond in enaminones for synthesis α-thiocyanoketones and 2-aminothiazoles. The reactions with ammonium thiocyanate provide ultrasound irradiation at room temperature. More interestingly, simply further heating vessel after ultrasonic leads selective 2-aminothiazoles an unconventional 4-aryl substructure.

Language: Английский

Citations

30

Synthesis of Chromone‐3‐phosphonates via Arbuzov‐Type C−P Cross Coupling from o‐Hydroxyphenyl Enaminones and Phosphites DOI

Dingsheng Cao,

Jie‐Ping Wan, Yunyun Liu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(17), P. 3670 - 3675

Published: July 2, 2024

Abstract With an in situ C−H iodination tactic, a method for the synthesis of chromone‐3‐phosphonates was developed with trialkyl/triaryl phosphites as reaction partners o ‐hydroxyphenyl enaminones by palladium catalysis. The product formation consists cascade iodination, chromone annulation, and Arbuzov‐type C−P cross coupling major transformations. In addition to providing enaminone‐based synthetic chromone‐3‐phosphonates, work shows advantage step economy skipping separate operation preparing iodo‐functionalized intermediate.

Language: Английский

Citations

6