76584-01-5Relevant academic research and scientific papers
Palladium-catalyzed reaction of γ-silylated allyl acetates proceeding through 1,2-shift of a substituent on silicon
Horino, Yoshikazu,Ishibashi, Mayo,Nakasai, Kosuke,Korenaga, Toshinobu
, (2020/08/28)
The palladium-catalyzed reaction of γ-silylated allyl acetates with water in the presence of CsF induces a previously unprecedented 1,2-shift of a substituent on silicon to produce allylsilanes in situ. The catalytic activity of the palladium increased when using an electron-poor phosphine ligand possessing fluorinated substituents. Further investigation of the reaction revealed that the approximate order of the migratory aptitude of groups from silicon was PhC≡C, allyl > Bn > Ph, vinyl > alkyl (Me, Et). A density functional theory study was employed to explore the reaction mechanism. Finally, the Hosomi–Sakurai-type allylation of aldehydes with in situ-generated α,γ-disubstituted allylsilanes was also investigated.
A photocatalyst-free photo-induced denitroalkylation of β-nitrostyrenes with 4-alkyl substituted Hantzsch esters at room temperature
Duan, Chunying,Hao, Xinyu,Jin, Kun,Li, Yaming,Wang, Jiaao,Zhang, Rong,Zhang, Siyu
, (2020/02/18)
A photocatalyst-free stereoselectively photo-induced strategy for the denitroalkylation of β-nitrostyrenes using 4-alkyl substituted Hantzsch esters as the alkyl source under xenon lamp irradiation is developed. The reaction proceeds at room temperature and affords the corresponding products in moderate to excellent yields. The oxidant di-t-butyl peroxide serves as an efficient radical initiator under irradiation of a Xenon lamp, initiating alkyl radicals from the 4-alkyl substituted Hantzsch esters.
Nickel-Catalyzed Direct Coupling of Allylic Alcohols with Organoboron Reagents
Wang, Gaonan,Gan, Yi,Liu, Yuanhong
, p. 916 - 920 (2018/09/22)
The direct coupling of allylic alcohols with arylboronic acids or their derivatives catalyzed by Ni(cod)2 in the presence of a catalytic amount of base has been developed. A wide variety of allylic substrates or arylboronic acids turned out to be applicable to this catalytic system. The present method does not require the use of ligands for stabilizing the nickel catalyst in most cases or additional activators for activation of allylic alcohols.
Copper-catalyzed oxidative alkenylation of C(sp3)-H bonds via benzyl or alkyl radical addition to β-nitrostyrenes
Guo, Shengrong,Yuan, Yanqin,Xiang, Jiannan
supporting information, p. 3093 - 3097 (2015/04/14)
A new method for the preparation of (E)-β-alkylstyrene derivatives has been developed via the addition of a benzyl or alkyl radical to β-nitrostyrenes using di-tert-butyl peroxide (DTBP) as the oxidant in the presence of Cu powder catalyst. The C-H bonds in various toluene derivatives, ethers, alkanes and alcohols were successfully converted into C-C bonds to yield the corresponding (E)-β-alkylstyrene derivatives in moderate to good yields.
Alkyl transfer from C-C cleavage: Replacing the nitro group of nitro-olefins
Li, Guangxun,Wu, Lei,Lv, Gang,Liu, Hongxin,Fu, Qingquan,Zhang, Xiaomei,Tang, Zhuo
supporting information, p. 6246 - 6248 (2014/06/09)
Alkyl substituted Hantzsch esters are rationally used as alkylation reagents to replace the nitro groups of nitro olefins to give excellent yields of trans-olefins. The reaction mechanism is considered to proceed through a free radical mechanism, which is different from the corresponding transfer alkylation of imines. This journal is the Partner Organisations 2014.
Iron-catalyzed direct alkenylation of sp3(C-H) bonds via decarboxylation of cinnamic acids under ligand-free conditions
Yang, Hailong,Yan, Hong,Sun, Peng,Zhu, Yan,Lu, Linhua,Liu, Defu,Rong, Guangwei,Mao, Jincheng
supporting information, p. 976 - 981 (2013/07/26)
An example of highly efficient low-cost ferrocene-catalyzed decarboxylative C(sp2)-C(sp3) coupling reactions via C-H functionalization has been developed successfully. It is noteworthy that nanoparticles of Fe3O4 could be used as a reusable catalyst for 7 times in the absence of ligand.
Cross-coupling of N-allylic sulfonimides with organozinc reagents at room temperature
Tang, Xiang-Ling,Wu, Zhao,Li, Man-Bo,Gu, Yonghong,Tian, Shi-Kai
supporting information; experimental part, p. 4107 - 4109 (2012/09/08)
An efficient cross-coupling reaction of N-allylic sulfonimides with organozinc reagents has been developed. In the presence of 1 mol-% of Pd 2(dba)3, a range of N-allylic sulfonimides smoothly couple with various organozinc reagents at room temperature to give the corresponding (E)-alkene products in moderate to excellent yields and with good to exclusive α-selectivity. It is noteworthy that allyl ether, benzyl ether, and ester are tolerated under the reaction conditions. A range of N-allylic sulfonimides smoothly couple with various organozinc reagents in the presence of 1 mol-% of Pd2(dba)3 at room temperature to give the corresponding (E)-alkene products in moderate to excellent yields and with good to exclusive α-selectivity.
Selective deoxygenation of allylic alcohol: Stereocontrolled synthesis of lavandulol
Kim, Hee Jin,Su, Liang,Jung, Heejung,Koo, Sangho
, p. 2682 - 2685 (2011/06/26)
Selective deoxygenation of allylic alcohol can be successfully carried out by the formation of alkoxyalkyl ether (EE or MOM), followed by Pd(dppe)Cl 2-catalyzed reduction with LiBHEt3. (+)-S-Lavandulol has been efficiently synthesized by the application of this protocol to the diol derived from the Pb(OAc)4-promoted oxidative ring-opening of (-)-R-carvone. This deoxygenation method is general and selective for allylic alcohols.
Iridium-catalyzed asymmetric allylic substitution with aryl zinc reagents
Alexakis, Alexandre,El Hajjaji, Samir,Polet, Damien,Rathgeb, Xavier
, p. 3393 - 3395 (2008/02/12)
Thanks to iridium catalysis, arylzinc reagents undergo regioselective allylic substitution with very high enantioselectivity, when associated with phosphoramidite ligands.
Cross-coupling reactions of allylic alcohols in water
Manabe, Kei,Nakada, Kenji,Aoyama, Naohiro,Kobayashi, Shu
, p. 1499 - 1503 (2007/10/03)
Palladium-catalyzed cross-coupling reactions of allylic alcohols and arylboronic acids in water are described. The reactions proceeded smoothly in water at reflux using catalytic amounts of [Pd(allyl)Cl]2 and PPh3. Addition of a catalytic amount of a base allowed the reaction to proceed even at lower temperatures.
