67082-95-5Relevant academic research and scientific papers
[4+2] or [4+1] Annulation: Changing the Reaction Pathway of a Rhodium-Catalyzed Process by Tuning the Cp Ligand
Hong, Seung Youn,Jeong, Jisu,Chang, Sukbok
, p. 2408 - 2412 (2017)
A change in reaction pathway was achieved for the first time by tuning the cyclopentadienyl (Cp) ligand used for the rhodium-catalyzed cyclization of benzamides with conjugated enynones. Depending on the Cp ligand, the reaction pathway switched between [4+2] and [4+1] annulation. Electronic effects turned out to be crucial for the product distribution. The dichotomy was attributed to the alteration of the Lewis acidity of the resultant Cp-bound rhodium species.
Preparation of 4-(Nitromethyl)furan Derivatives and Their Application in the Syntheses of Bis(furan-2-yl)oximes
Wan, Yinbo,Zhu, Yang,Peng, Haiyun,Deng, Guisheng
, p. 281 - 293 (2021/12/27)
An efficient method for the preparation of tetrasubstituted furans, which contains a nitromethyl group at the 4-position, has been developed. The applications of 4-(nitromethyl)furans on the synthesis of highly functionalized bis(furyl)oxime were explored
Synthesis of C3-alkenylated 2,3,4-trisubstituted pyrrole derivatives through cyclization of methylene isocyanides and ene-yne-ketones
Li, Shasha,Zeng, Gongruixue,Xing, Xiaoqi,Yang, Zhiheng,Ma, Feiyun,Li, Boxia,Cheng, Weiyan,Zhang, Jiankang,He, Ruoyu
supporting information, p. 1834 - 1837 (2021/02/06)
A mild, transition-metal-free and facile C3-alkenylated 2,3,4-trisubstituted pyrrole cyclization of methylene isocyanides with ene-yne-ketones in moderate to good yields was explored. The E-alkenylated products were isolated in moderate to exclusive selec
AgOTf/I2-Mediated Cyclization/Cross-Coupling/Isomerization of Enynones with Phosphorus Ylides: An Expedient Route to Stereoselective Synthesis of (E)-2-Alkenylfurans
Deng, Guisheng,Tang, Ling,Zhang, Yangyi
, p. 13245 - 13251 (2021/10/01)
Ag(I)-catalyzed cascade reactions involving enynone cyclization and cross-coupling with phosphorus ylides have been achieved for the first time. Subsequent treatment of the reaction mixture with I2 afforded the corresponding (E)-α-alkenylfurans in 73-95%
CuOTf/TfOH-mediated tandem reaction of conjugated ene-yne-ketones: Synthesis of novel spiro dihydrofurans
Yang, Qin,Zhu, Yang,Deng, Guisheng
supporting information, (2020/09/04)
CuOTf/TfOH-mediated cascade cyclization-coupling-electrophilic substitution of conjugated ene-yne-ketones in DCE at 25 °C provided novel spiro dihydrofurans in 32–83% yield. The experimental results demonstrated that substituent group R3, which
Access to Polysubstituted (Furyl)methylthioethers via a Base-Promoted S-H Insertion Reaction of Conjugated Enynones
Wu, Wanqing,Chen, Yang,Li, Meng,Hu, Weigao,Lin, Xuemin
, p. 14529 - 14539 (2019/11/11)
A convenient and applicable approach to the construction of diverse functionalized (2-furyl)methylthioether derivatives via base-promoted S-H insertion of conjugated enynones with thiophenols or thiols has been developed. This reaction features readily av
Mechanistic Divergence in the Hydrogenative Synthesis of Furans and Butenolides: Ruthenium Carbenes Formed by gem-Hydrogenation or through Carbophilic Activation of Alkynes
Peil, Sebastian,Fürstner, Alois
supporting information, p. 18476 - 18481 (2019/11/14)
Enynes with a tethered carbonyl substituent are converted into substituted furan derivatives upon hydrogenation using [Cp*RuCl]4 as the catalyst. Paradoxically, this transformation can occur along two distinct pathways, each of which proceeds via discrete pianostool ruthenium carbenes. In the first case, hydrogenation and carbene formation are synchronized (“gem-hydrogenation”), whereas the second pathway comprises carbene formation by carbophilic activation of the triple bond, followed by hydrogenative catalyst recycling. Representative carbene intermediates of either route were characterized by X-ray crystallography; the structural data prove that the attack of the carbonyl group on the electrophilic carbene center follows a Bürgi–Dunitz trajectory.
Base-Promoted Tandem Cyclization for the Synthesis of Benzonitriles by C?C Bond Construction
Zhu, Cheng-Zhi,Wei, Yin,Shi, Min
supporting information, p. 808 - 813 (2018/01/27)
A facile synthesis of benzonitriles via a base-promoted tandem cyclization reaction of α,β-unsaturated enones having electron-withdrawing group (EWG) and 2-acyl-acrylonitriles was developed. This new synthetic method to access benzonitriles is suitable for a wide range of substrates. A plausible reaction mechanism is proposed on the basis of previous literature and our own investigations. (Figure presented.).
Facile synthesis of cyanofurans via Michael-addition/cyclization of ene-yne-ketones with trimethylsilyl cyanide
Yu, Yue,Chen, Yang,Wu, Wanqing,Jiang, Huanfeng
supporting information, p. 640 - 643 (2017/01/13)
We have developed a Michael-addition/cyclization procedure between ene-yne-ketones and TMSCN under metal-free conditions. A wide range of cyanofurans was delivered in high yields, which could be further transformed to a series of furo-furanimines, furo-pyridazines or carboxamido-furans. In addition, deuterium-labeling experiments have been conducted to clarify the reaction pathway.
Phosphine-Mediated Dimerization of Conjugated Ene-Yne Ketones: Stereoselective Construction of Dihydrobenzofurans
Zhu, Cheng-Zhi,Sun, Yao-Liang,Wei, Yin,Shi, Min
supporting information, p. 1263 - 1270 (2017/04/18)
A new strategy for the phosphine-mediated dimerization of conjugated ene-yne ketones to produce functionalized dihydrobenzofurans has been developed, affording diversified 4,5-dihydrobenzofurans in moderate to excellent yields with high diastereoselectivities under mild conditions. This new synthetic method can tolerate a variety of functional groups and can be performed on a gram scale and in an asymmetric variant using the chiral phosphine Xyl-BINAP to give the desired products with up to 94% ee. (Figure presented.).
