103499-84-9Relevant academic research and scientific papers
Selective [5,5]-Sigmatropic Rearrangement by Assembly of Aryl Sulfoxides with Allyl Nitriles
Zhang, Lei,He, Jia-Ni,Liang, Yuchen,Hu, Mengjie,Shang, Li,Huang, Xin,Kong, Lichun,Wang, Zhi-Xiang,Peng, Bo
, p. 5316 - 5320 (2019)
Aromatic [5,5]-sigmatropic rearrangement is an appealing protocol for accessing 1,4-substituted arenes. However, such a protocol has not been well utilized in organic synthesis because of the difficulties in the synthesis of the substrates, selectivity issues, and limited substrate scope. Described herein is a new [5,5]-sigmatropic reaction utilizing readily available aryl sulfoxides and allyl nitriles. This reaction features mild reaction conditions, high chemo- and regioselectivity, excellent functional-group compatibility, and broad substrate scope. Computational studies suggest that the success of the reaction can be attributed to the selective electrophilic assembly of the rearrangement precursors, in which a linear -C=C=N- linkage favors [5,5]-sigmatropic rearrangement over the competitive [3,3]-sigmatropic rearrangement.
Copper-Catalyzed Regioselective Allylic Cyanation of Allylic Compounds with Trimethylsilyl Cyanide
Munemori, Daisuke,Tsuji, Hiroaki,Uchida, Kenta,Suzuki, Tomoaki,Isa, Kazuki,Minakawa, Maki,Kawatsura, Motoi
, p. 2747 - 2750 (2015/10/28)
The copper-catalyzed regioselective allylic cyanation of allylic compounds with trimethylsilyl cyanide (TMSCN) is described. Copper(I) iodide (CuI), copper(I) cyanide (CuCN) and copper(II) chloride (CuCl2) are shown to effectively catalyze the cyanation of various allylic substrates to afford the corresponding allylic cyanides in good yields and high regioselectivities. The reaction in the presence of 2,2,6,6-tetramethyl-1-piperidinyloxy free radical (TEMPO) reveals that the cyanation proceeds via a radical pathway.
Base-Induced α-Alkenylation of Ethyl Bromoacetate, Phenacyl Bromide, and Chloroacetonitrile via B-trans -1-Alkenyl-9-borabicyclononanes
Brown, Herbert C.,Bhat, Narayan G.,Campbell, James B.
, p. 3398 - 3400 (2007/10/02)
B-trans-1-Alkenyl-9-borabicyclononanes, easily and quantitatively prepared by the reaction of 9-BBN with various 1-alkynes in tetrahydrofuran, undergo facile reaction with α-halo carbanions generated from ethyl bromoacetate, phenacyl bromide, and c
