23848-95-5Relevant academic research and scientific papers
A 1,4-Palladium Migration/Heck Sequence with Unactivated Alkenes: Stereoselective Synthesis of Trisubstituted 1,3-Dienes
Xue, Ze-Jian,Li, Meng-Yao,Zhu, Bin-Bin,He, Zhi-Tao,Feng, Chen-Guo,Lin, Guo-Qiang
supporting information, p. 2089 - 2092 (2021/03/08)
The palladium-catalyzed cross-coupling of ortho-vinyl aromatic bromides and olefins was achieved through a controllable 1,4-palladium migration/Heck cascade protocol. The reaction represents a mild, efficient and highly stereoselective method for the synthesis of trisubstituted 1,3-dienes, especially for triaryl-substituted ones. (Figure presented.).
Z -Selective iridium-catalyzed cross-coupling of allylic carbonates and α-diazo esters
Thomas, Bryce N.,Moon, Patrick J.,Yin, Shengkang,Brown, Alex,Lundgren, Rylan J.
, p. 238 - 244 (2018/01/02)
A well-defined Ir-allyl complex catalyzes the Z-selective cross-coupling of allyl carbonates with α-aryl diazo esters. The process overrides the large thermodynamic preference for E-products typically observed in metal-mediated coupling reactions to enable the synthesis of Z,E-dieneoates in good yield with selectivities consistently approaching or greater than 90:10. This transformation represents the first productive merger of Ir-carbene and Ir-allyl species, which are commonly encountered intermediates in allylation and cyclopropanation/E-H insertion catalysis. Potentially reactive functional groups (aryl halides, ketones, nitriles, olefins, amines) are tolerated owing to the mildness of reaction conditions. Kinetic analysis of the reaction suggests oxidative addition of the allyl carbonate to an Ir-species is rate-determining. Mechanistic studies uncovered a pathway for catalyst activation mediated by NEt3.
Pd(0)-catalyzed cross-coupling of allyl halides with α-diazocarbonyl compounds or N-mesylhydrazones: Synthesis of 1,3-diene compounds
Wang, Kang,Chen, Shufeng,Zhang, Hang,Xu, Shuai,Ye, Fei,Zhang, Yan,Wang, Jianbo
, p. 3809 - 3820 (2016/05/09)
With palladium catalysis, allyl bromides or chlorides react with α-diazocarbonyl compounds or N-mesylhydrazones to afford 1,3-diene derivatives. The reaction represents a novel and efficient method for the synthesis of 1,3-butadiene derivatives. Mechanist
Palladium(II)/Lewis acid synergistically catalyzed allylic C-H olefination
Wang, Pu-Sheng,Lin, Hua-Chen,Zhou, Xiao-Le,Gong, Liu-Zhu
, p. 3332 - 3335 (2014/07/08)
The first allylic C-H olefination with α-diazo esters synergistically catalyzed by a palladium(II) complex and (salen)CrCl has been established to directly generate conjugated polyene derivatives in moderate to high yields and with excellent stereoselectivities.
Palladium-catalyzed reaction of allyl halides with α-diazocarbonyl compounds
Chen, Shufeng,Wang, Jianbo
supporting information; scheme or table, p. 4198 - 4200 (2009/03/11)
The Pd(OAc)2-catalyzed reaction between α-diazocarbonyl compounds and allyl bromides or chlorides leads to the formation of 1,3-diene derivatives. The Royal Society of Chemistry.
