119405-98-0Relevant academic research and scientific papers
Palladium-catalysed hydrostannylations of 1-bromoalkynes. A practical synthesis of (E)-1-stannylalk-1-enes
Boden, Christopher D. J.,Pattenden, Gerald,Ye, Tao
, p. 2417 - 2419 (1996)
A practical synthesis of (E)-1-stannylalk-1-enes containing a range of oxygen and nitrogen functionality is highlighted, involving hydrostannylation followed by palladium-catalysed carbon-bromine bond cleavage reactions of 1-bromoalkynes.
Benzannulation of triynes to generate functionalized arenes by spontaneous incorporation of nucleophiles
Karmakar, Rajdip,Yun, Sang Young,Chen, Jiajia,Xia, Yuanzhi,Lee, Daesung
supporting information, p. 6582 - 6586 (2015/06/02)
The thermal reaction of ester-tethered 1,3,8-triynes provides novel benzannulation products with concomitant incorporation of a nucleophile. Evidence suggests that this reaction proceeds via an allene-enyne intermediate generated by an Alder-ene reaction in the first step. Depending on the substituent of the alkyne moiety on the allene-enyne intermediate, the subsequent transformation can take one of two different paths, each leading to discrete aromatization products. The benzannulation of a silane-substituted 1,3,8-triynes provides arene products with a nucleophile incorporated onto the newly formed benzene core, whereas an aryl substituent leads to nucleophile trapping at the benzylic carbon atom connected to the aryl substituent. The formation of these two different products results from the involvement of two regioisomeric allene-enyne intermediates.
Reactions of 1,1-Dihaloalkenes with Triorganozincates: A Novel Method for the Preparation of Alkenylzinc Species Associated with Carbon-Carbon Bond Formation
Harada, Toshiro,Katsuhira, Takeshi,Hara, Daiji,Kotani, Yasuo,Maejima, Keiji,et al.
, p. 4897 - 4907 (2007/10/02)
Lithium trialkylzincates react with 1,1-dibromoalkenes 1 and 1-bromo-1-chloroalkenes 2 at -85 deg C in THF to give 1-bromoalkenes 5 and 1-chloroalkenes 7, respectively, upon hydrolysis.The intermediate (1-haloalkenyl)zincates 4 and 6 are stable at low temperature but, when allowed to warm to 0 deg C, they undergo a 1,2-alkyl migration reaction to afford alkenylzinc species 10.A variety of alkylation products 11 are obtained by the hydrolysis of 10.In the presence of (Ph3P)2Pd (5 molpercent), alkenylzinc species 10 react smoothly with organic halides (AcCl, EtOCOCl, CH2=CH(Me)Br, PhBr) to yield the corresponding coupling products 13-16.
