233672-87-2Relevant academic research and scientific papers
Nickel-catalyzed anti-Markovnikov hydroarylation of alkenes
Nguyen, Julia,Chong, Andrea,Lalic, Gojko
, p. 3231 - 3236 (2019/03/21)
We have developed a nickel-catalyzed hydroarylation of alkenes using aryl halides as coupling partners. Excellent anti-Markovnikov selectivity is achieved with aryl-substituted alkenes and enol ethers. We also show that hydroarylation occurs with alkyl substituted alkenes to yield linear products. Preliminary examination of the reaction mechanism suggests irreversible hydrometallation as the selectivity determining step of the hydroarylation.
Transition-Metal-Free Sulfuration/Annulation of Alkenes: Economical Access to Thiophenes Enabled by the Cleavage of Multiple C-H Bonds
Chen, Liang,Min, Hao,Zeng, Weilan,Zhu, Xiaoming,Liang, Yun,Deng, Guobo,Yang, Yuan
supporting information, p. 7392 - 7395 (2019/01/03)
A novel, atom economical, and transition-metal-free strategy for the synthesis of thiophenes from substituted buta-1-enes with potassium sulfide has been presented. The reaction achieves double C-S bond formations via cleavage of multiple C-H bonds and provides an efficient approach to access various functionalized thiophenes. Moreover, the strategy can also be used for the synthesis of thiophenes from 1,4-diaryl-1,3-dienes. Mechanistically, DMSO plays a role of oxidant and S3?- in situ generated from K2S is involved.
CaII-Catalyzed Alkenylation of Alcohols with Vinylboronic Acids
Leb?uf, David,Presset, Marc,Michelet, Bastien,Bour, Christophe,Bezzenine-Lafollée, Sophie,Gandon, Vincent
supporting information, p. 11001 - 11005 (2015/11/10)
Direct alkenylation of a variety of alcohols with vinylboronic acids has been accomplished using the air-stable calcium(II) complex Ca(NTf2)2 under mild conditions with short reaction times. For reluctant transformations, an ammonium salt was used as an additive to circumvent the reactivity issue. Cross-coupling: Direct alkenylation of a variety of alcohols with vinylboronic acids has been accomplished using the air-stable calcium(II) complex Ca(NTf2)2 under mild conditions with short reaction times (see scheme)
A novel efficient method for the synthesis of substituted olefins; Cross coupling of two different alcohols using NaHSO4/SiO2
Aoyama, Tadashi,Koda, Shuichi,Takeyoshi, Yuka,Ito, Tetsuhiro,Takido, Toshio,Kodomari, Mitsuo
, p. 6605 - 6607 (2013/07/26)
Simple and efficient cross coupling of alcohols was developed in the presence of NaHSO4/SiO2 to give the corresponding substituted olefins. Direct coupling of alcohols and alkenes was also achieved to give substituted olefins. NaHSO4/SiO2 could be recycled 7 times without loss of catalytic activity.
Versatile friedel-crafts-type alkylation of benzene derivatives using a molybdenum complex/ortho-chloranil catalytic system
Yamamoto, Yoshihiko,Itonaga, Kouhei
experimental part, p. 10705 - 10715 (2009/12/01)
A variety of molybdenum complexes catalyze Friedel-Crafts-type alkylation reactions of benzene derivatives with alkenes and alcohols in the presence of an organic oxidant, o-chloranil. The utilization of [Mo(CO)6] and two equivalents of o-chloranil catalytically furnished the hydroarylation product of norbornene with p-xylene at 80°C, whereas [Cr(CO)6] and [W(CO)6] failed to catalyze the same reaction, thus indicating the importance of the molybdenum source. The best results were obtained when a molybdenum(II) complex [CpMoCl(CO)3] (Cp = cyclopentadienyl) was used as a precatalyst. The hydroarylation reactions also took place with styrenes, cyclohexenes, and 1 -hexene as olefin substrates. The electrophilic-substitution mechanism was proposed on the basis of the ortho/para selectivities and the Markovnikov selectivities observed for the hydroarylation products. Our hypothesis was further corroborated by the fact that in the presence of the [CpMoCl(CO)3]/o-chloranil catalytic system, secondary, benzylic, or allylic alcohols participated in the alkylation of benzenes with similar selectivities.
