119405-99-1Relevant academic research and scientific papers
Stereoselective Synthesis of Vinyl Iodides through Copper(I)-Catalyzed Finkelstein-Type Halide-Exchange Reaction
Feng, Xiujuan,Zhang, Haixia,Lu, Wenbo,Yamamoto, Yoshinori,Almansour, Abdulrahman I.,Arumugam, Natarajan,Kumar, Raju Suresh,Bao, Ming
supporting information, p. 2727 - 2732 (2017/06/13)
An efficient method for the stereoselective synthesis of vinyl iodides is described. The reactions of vinyl bromides with potassium iodide proceed smoothly in the presence of a copper catalyst under mild reaction conditions to produce the corresponding vinyl iodides stereospecifically and in satisfactory to excellent yields.
Stereochemistry in carbenoid formation by bromine/lithium and bromine/zinc exchange reactions of gem-dibromo compounds
Harada, Toshiro,Katsuhira, Takeshi,Hattori, Kazuhiro,Oku, Akira
, p. 7987 - 8002 (2007/10/02)
Stereochemistry in generation of lithium and zincate carbenoids by bromine/metal exchange reactions of gem-dibromo compounds with BuLi and lithium triorganozincates, respectively, has been investigated. Both lithium and zincate carbenoids derived from 1,1
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.
Stereochemistry in Carbenoid Formation by Bromine/Lithium and Bromine/Zinc Exchange Reactions of 1,1-Dibromoalkenes: Higher Reactivity of the Sterically More Hindered Bromine Atom
Harada, Toshiro,Katsuhira, Takeshi,Oku, Akira
, p. 5805 - 5807 (2007/10/02)
Both lithium and zincate carbenoids (R1(R2)C=C(Br)M; M = Li and Zn(Bu)2Li) generated by the halogen/metal exchange reaction of 1,1-dibromoalkene 1 with BuLi and (Bu)3ZnLi, respectively, are configurationally stable at low temperature
GENERATION AND ALKYLATION REACTION OF 1-BROMOALKENYLZINCATE
Harada, Toshiro,Hara, Daiji,Hattori, Kazuhiro,Oku, Akira
, p. 3821 - 3824 (2007/10/02)
1-Bromoalkenylzincates (R1R2C=CBrZnR32Li) which are generated by the reaction of 1,1-dibromoalkenes with a lithium triorganozincate (R33ZnLi) at -85 deg C undergo alkylation reaction at temperatures from -85 deg C to 0 deg C to give alkenes R1R2C=CHR3.
