59409-55-1Relevant academic research and scientific papers
A convenient access to allylic triflones with allenes and triflyl chloride in the presence of (EtO)2P(O)H
Ni, Jixiang,Jiang, Yong,An, Zhenyu,Lan, Jingfeng,Yan, Rulong
, p. 7343 - 7345 (2019/06/27)
A simple method for the preparation of allylic triflones from allenes and triflyl chloride in the presence of (EtO)2P(O)H has been developed. The features of this reaction are catalyst-free and simple starting substrates. This method tolerates diverse functional groups and substituted allylic triflones are obtained in moderate to good yields.
Construction of All-Carbon Chiral Quaternary Centers through CuI-Catalyzed Enantioselective Reductive Hydroxymethylation of 1,1-Disubstituted Allenes with CO2
Qiu, Jia,Gao, Shen,Li, Chaopeng,Zhang, Lei,Wang, Zheng,Wang, Xiaoming,Ding, Kuiling
, p. 13874 - 13878 (2019/11/11)
A catalytic enantioselective construction of all-carbon chiral quaternary centers through reductive hydroxymethylation of 1,1-disubstituted allenes with CO2 has been developed. In the presence of a copper/Mandyphos catalyst, CO2 is t
Chlorination of phenylallene derivatives with 1-chloro-1,2-benziodoxol-3-one: Synthesis of vicinal-dichlorides and chlorodienes
Zhao, Zhensheng,Murphy, Graham K.
, p. 796 - 802 (2018/04/16)
Allyl and vinyl chlorides represent important structural motifs in organic chemistry. Herein is described the chemoselective and regioselective reaction of aryl- and α-substituted phenylallenes with the hypervalent iodine (HVI) reagent 1-chloro-1,2-benz-iodoxol-3-one. The reaction typically results in vicinal dichlorides, except with proton-containing α-alkyl substituents, which instead give chlorinated dienes as the major product. Experimental evidence suggests that a radical mechanism is involved.
Fluorinative Rearrangements of Substituted Phenylallenes Mediated by (Difluoroiodo)toluene: Synthesis of α-(Difluoromethyl)styrenes
Zhao, Zhensheng,Racicot, Léanne,Murphy, Graham K.
, p. 11620 - 11623 (2017/09/11)
Phenylallenes undergo fluorinative rearrangement upon the action of (difluoroiodo)toluene in the presence of 20 mol % BF3?OEt2 to yield α-difluoromethyl styrenes. This unprecedented reaction was entirely chemoselective for the internal allene π bond, and showed remarkable regioselectivity during the fluorination event. Substituted phenylallenes, phenylallenes possessing both phenyl- and α-allenyl substituents, and diphenylallenes were investigated, and good functional-group compatibility was observed throughout. The ease with which allenes can be prepared on a large scale, and the operational simplicity of this reaction allowed us to rapidly access fluorine-containing building blocks that have not been accessed by conventional deoxyfluorination strategies.
Iodothiocyanation/Nitration of Allenes with Potassium Thiocyanate/Silver Nitrite and Iodine
Yang, Xiaodong,She, Yue,Chong, Ya,Zhai, Huichun,Zhu, He,Chen, Baohua,Huang, Guosheng,Yan, Rulong
, p. 3130 - 3134 (2016/10/09)
Direct strategies for the iodothiocyanation and iodonitration of allenes have been developed. In this process, potassium thiocyanate/silver nitrite and molecular iodine are used as the source of SCN, ONO2and iodine to provide the desired products in moderate to good yields with high stereoselectivity. (Figure presented.).
Nickel-catalyzed substitution reactions of propargyl halides with organotitanium reagents
Li, Qing-Han,Liao, Jung-Wei,Huang, Yi-Ling,Chiang, Ruei-Tang,Gau, Han-Mou
, p. 7634 - 7642 (2014/12/11)
A simple and mild catalytic coupling reaction of propargyl halides with organotitanium reagents is reported. The reaction of propargyl bromide with organo-titanium reagents mediated by NiCl2(2 mol%) and PCy3(4 mol%) in CH2
Catalytic enantioselective protoboration of disubstituted allenes. Access to alkenylboron compounds in high enantiomeric purity
Jang, Hwanjong,Jung, Byunghyuck,Hoveyda, Amir H.
, p. 4658 - 4661 (2015/02/19)
Proto-boryl additions to 1,1-disubstituted allenes in the presence of 1.0-5.0 mol % of chiral NHC-Cu complexes, B2(pin)2, and t-BuOH proceed to afford alkenyl-B(pin) products in up to 98% yield, >98:2 site selectivity, and 98:2 er. T
Synthesis of allenes via Nickel-catalyzed cross-coupling reaction of propargylic bromides with grignard reagents
Li, Qinghan,Gau, Hanmou
experimental part, p. 747 - 750 (2012/06/29)
We describe a convenient method for the synthesis of terminal allenes from cross-coupling of propargylic bromide with Grignard reagent. The reaction of propargylic bromide with 1.2 equivalents of Grignard reagent mediated by Ni(acac)2 (2 mol%) and Ph3P (4 mol%) in THF may produce terminal allenes in good yields and high regioselectivities at room temperature. Georg Thieme Verlag Stuttgart · New York.
Studies on Cu(I)-catalyzed synthesis of simple 3-substituted 1,2-allenes and optically active 2-substituted secondary 2,3-allenols
Li, Jing,Zhou, Chao,Fu, Chunling,Ma, Shengming
experimental part, p. 3695 - 3703 (2009/09/05)
The sequential treatment of terminal alkynes or propargylic alcohols with n-BuLi and MOMCl afforded the corresponding propargylic methyl ethers, which would react with primary alkyl Grignard reagents under the catalysis of CuBr to afford 3-substituted 1,2-allenes or 2-substituted secondary 2,3-allenols, respectively. The reaction may be applied to the synthesis of optically active 2-substituted secondary 2,3-allenols with up to >99% ee without any protection to the free hydroxyl group in the starting 4-hydroxy-2-alkynyl methyl ethers.
Organozinc reagents in DMSO solvent: Remarkable promotion of S N2′ reaction for allene synthesis
Kobayashi, Koji,Naka, Hiroshi,Wheatley, Andrew E. H.,Kondo, Yoshinori
supporting information; experimental part, p. 3375 - 3377 (2009/05/30)
(Chemical Equation Presented) The SN2′ reaction of propragyl mesylates with organozinc reagents was dramatically improved in DMSO solvent, and the stereoselective conversion of chiral substrates was successfully achieved using LiCl-free diorgan
