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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Selective 1,2-Aminoisothiocyanation of 1,3-Dienes Under Visible-Light Photoredox Catalysis
Guo, Weisi,Wang, Qian,Zhu, Jieping
supporting information, p. 4085 - 4089 (2020/12/25)
Selective three-component 1,2-diamination of 1,3-dienes with concurrent introduction of two orthogonally protected amino groups remains unknown despite its significant synthetic potential. We report herein that reaction of conjugated dienes with N-aminopy
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,