16939-57-4Relevant articles and documents
A convenient method for the synthesis of terminal (E)-1,3-dienes
Wang,West
, p. 99 - 103 (2002)
Lithiated allylic phosphonates undergo efficient olefination reactions with a variety of aldehydes in the presence of HMPA to give terminal 1,3-dienes with high selectivity for the E-isomer. This method is general and procedurally simple.
Catalyst Controlled Regiodivergent Arylboration of Dienes
Sardini, Stephen R.,Brown, M. Kevin
, p. 9823 - 9826 (2017)
A method for the regiodivergent arylboration of dienes is presented. These reactions allow for the formation of a diverse range of synthetically versatile products from simple precursors. Through mechanistic studies, these reactions likely operate by init
A STEREO- AND REGIO-SPECIFIC ADDITION OF ν3-TRIMETHYLSILYLALLYLTITANIUM COMPOUND WITH ALDEHYDES. A FACILE AND STEREOCONTROLLED SYNTHESIS OF E- AND Z-TERMINAL DIENES
Sato, Fumie,Suzuki, Yoshito,Sato, Masao
, p. 4589 - 4592 (1982)
ν3-Trimethylsilylallyltitanium compound, (ν5-C5H5)2Ti(ν3-1-trimethylsilylallyl), reacts with aldehydes to give (+/-)-(R,S)-3-trimethylsilyl-4-hydroxy-1-alkenes in excellent yields, which can be deoxysilylated to either E- or Z-1,3-dienes.
Copolymerization of 1,3-butadiene with phenyl/phenethyl substituted 1,3-butadienes: a direct strategy to access pendant phenyl functionalized polydienes
Li, Dexin,Lin, Juan,Liu, Heng,Wang, Feng,Zhang, Chunyu,Zhang, Xuequan
, p. 23184 - 23191 (2021)
Copolymerization of 1,3-butadiene with various types of phenyl substituted 1,3-butadiene derivatives, including (E)-1-phenyl-1,3-butadiene (PBD), 1-phenethyl-1,3-butadiene (PEBD), 1-(4-methoxylphenyl)-1,3-butadiene (p-MEPBD), 1-(2-methoxylphenyl)-1,3-buta
Synthesis and heck reactions of ethenyl- and (Z)-butadien-1-yl nonaflate obtained by the fragmentation of furan derivatives
Lyapkalo, Ilya M.,Webel, Matthias,Reissig, Hans-Ulrich
, p. 4189 - 4194 (2001)
The nonaflation of lithium enolates or of silyl enol ethers, formally derived from acetaldehyde or crotonaldehyde, with nonafluorobutanesulfonyl fluoride gave ethenyl nonaflate (1b) and (Z)-buta-1,3-dien-1-yl nonaflate (2) in good yields. The required enolates were obtained by aldehyde-free routes by the lithiation of tetrahydrofuran or 2,5-dihydrofuran followed by the cyclofragmentation of the metallated heterocycles. The application of this approach to the synthesis of allenyl nonaflate 3 failed, presumably due to the intrinsic instability of this allene derivative. The nonaflates 1b and 2 were also prepared by the fluoride-catalysed reaction of the corresponding silyl enol ethers 5 and 7 with nonafluorobutanesulfonyl fluoride; however, the overall yields are slightly lower for these two-step pathways. The cyclofragmentation of lithiated 2,2-dimethyl-4-methylene-[1,3]dioxolane allowed the easy preparation of trimethylsiloxyallene (10) in moderate yield. The nonaflates 1b and 2 reacted smoothly with monosubstituted alkenes in the presence of a catalytic amount of palladium(II) acetate to give the anticipated Heck coupling products in good to moderate yields and with high stereoselectivities.
A Diverted Aerobic Heck Reaction Enables Selective 1,3-Diene and 1,3,5-Triene Synthesis through C-C Bond Scission
McAlpine, Neil J.,Wang, Long,Carrow, Brad P.
, p. 13634 - 13639 (2018)
Substituted 1,3-dienes are valuable synthetic intermediates used in myriad catalytic transformations, yet modern catalytic methods for their preparation in a highly modular fashion using simple precursors are relatively few. We report here an aerobic boron Heck reaction with cyclobutene that forms exclusively linear 1-aryl-1,3-dienes using (hetero)arylboronic acids, or 1,3,5-trienes using alkenylboronic acids, rather than typical Heck products (i.e., substituted cyclobutenes). Experimental and computational mechanistic data support a pericyclic mechanism for C-C bond cleavage that enables the cycloalkene to circumvent established limitations associated with diene reagents in Heck-type reactions.
Dynamic kinetic resolution of acyclic allylic acetates using lipase and palladium
Choi, Yoon Kyung,Suh, Jong Hwa,Lee, Donghyun,Lim, In Taek,Jung, Jae Yoon,Kim, Mahn-Joo
, p. 8423 - 8424 (1999)
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Ni-Catalyzed Regioselective Hydroarylation of 1-Aryl-1,3-Butadienes with Aryl Halides
Wang, Chengdong,Guo, Yingjie,Wang, Xiaoming,Wang, Zheng,Ding, Kuiling
supporting information, p. 15903 - 15907 (2021/10/07)
An efficient nickel-catalyzed regioselective hydroarylation of 1,3-dienes with aryl halides and a silane has been developed, affording a range of allylic arenes in good to excellent yields under mild conditions. This method exhibits broad substrate scope,
Electrochemistry enabled selective vicinal fluorosulfenylation and fluorosulfoxidation of alkenes
Jiang, Yimin,Shi, Zhaojiang,Wu, Jinnan,Wu, Shaofen,Ye, Keyin,Yu, Yi,Yuan, Yaofeng
supporting information, (2021/11/17)
Both sulfur and fluorine play important roles in organic synthesis, the life science, and materials science. The direct incorporation of these elements into organic scaffolds with precise control of the oxidation states of sulfur moieties is of great significance. Herein, we report the highly selective electrochemical vicinal fluorosulfenylation and fluorosulfoxidation reactions of alkenes, which were enabled by the unique ability of electrochemistry to dial in the potentials on demand. Preliminary mechanistic investigations revealed that the fluorosulfenylation reaction proceeded through a radical-polar crossover mechanism involving a key episulfonium ion intermediate. Subsequent electrochemical oxidation of fluorosulfides to fluorosulfoxides were readily achieved under a higher applied potential with the adventitious H2O in the reaction mixture.
