3864-19-5Relevant articles and documents
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.
supporting information, p. 13634 - 13639 (2018/10/24)
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.
Olefin-Migrative Cleavage of Cyclopropane Rings through the Nickel-Catalyzed Hydrocyanation of Allenes and Alkenes
Hori, Hiroto,Arai, Shigeru,Nishida, Atsushi
, p. 1170 - 1176 (2017/04/13)
A nickel-catalyzed hydrocyanation triggered by hydronickelation of the carbon-carbon double bonds of allenes followed by cyclopropane cleavage is described. The observed regio- and stereochemistries in the products are strongly influenced by the initial hydronickelation step, and allenyl- and methylenecyclopropanes reacted smoothly to promote the cleavage of cyclopropane. In contrast, this cleavage was not observed with vinylidenecyclopropanes, because the initial hydronickelation does not give a suitable intermediate for cleavage of the cyclopropanes. (Figure presented.).
A new protocol for nickel-catalysed regio- and stereoselective hydrocyanation of allenes
Arai, Shigeru,Hori, Hiroto,Amako, Yuka,Nishida, Atsushi
supporting information, p. 7493 - 7496 (2015/05/04)
Regio- and stereoselective hydrocyanation under nickel catalysis is described. This report shows that allenyl C-C double bonds are discriminated and converted to the corresponding carbonitriles as a single product. The key functionalities for achieving high regio- and stereocontrol are aryl and cyclopropyl groups in the substrates. This journal is
Synthesis of conjugated dienes and polyenes via diethyl phosphite promoted carbonyl olefination
Wang, Ru,Zhang, Songlin
, p. 39497 - 39507 (2014/11/08)
A protocol has been developed for the synthesis of conjugated dienes and polyenes from unsaturated carbonyl compounds and Grignard reagents in the presence of diethyl phosphite. This reaction was conveniently carried out under mild conditions in a one-pot fashion with moderate to good yields.
An approach to the regioselective diamination of conjugated di- and trienes
Lishchynskyi, Anton,Muniz, Kilian
, p. 2212 - 2216 (2012/03/27)
It's do or diaminate: The selective diamination of 1,3-butadienes in the presence of hypervalent iodine reagents has been developed. This oxidation process proceeds with complete selectivity in favor of diamination. Depending on the substrate, it proceeds either with 1,2- or 1,4-regioselectivity (see scheme). Copyright
Aqueous Wittig reactions of semi-stabilized ylides. A straightforward synthesis of 1,3-dienes and 1,3,5-trienes
McNulty, James,Das, Priyabrata
experimental part, p. 5737 - 5740 (2009/12/06)
A direct synthesis of 1,3-dienes and 1,3,5-trienes from the reaction of semi-stabilized ylides and a range of saturated and unsaturated aldehydes is reported in water as solvent, employing sodium hydroxide as base. The water-soluble phosphine oxide side p
A convenient one-pot synthesis of homoallylic halides and 1,3-butadienes
Wong, Ken-Tsung,Hung, Ying-Yueh
, p. 8033 - 8036 (2007/10/03)
An efficient one-pot synthetic pathway for the preparation of homoallylic halides by in situ generated MgBrCl-promoted ring opening of cyclopropylcarbinyl acetates has been established. An easily accessible one-pot synthetic protocol of 1,3-butadienes by the elimination of hydrogen halides from the resulting homoallylic halides in the presence of an excess amount of strong base has also been developed.
Stereoselective Synthesis of Substituted 1,3,5-Hexatrienes from Diallylic Sulfones
Cao, Xiao-Ping,Chan, Tze-Lock,Chow, Hak-Fun,Tu, Jingren
, p. 1297 - 1300 (2007/10/02)
Substituted 1,3,5-hexatrienes 7 can be prepared in excellent yields and with good stereoselectivity from diallylic sulfones 6 employing a modified Ramberg-Baecklund reaction.
Generation of Allylic and Related Organozirconiums Through A Highly Effective Zirconium-β-Alkoxide Elimination Reaction
Ito, Hisanaka,Nakamura, Takanori,Taguchi, Takeo,Hanzawa, Yuji
, p. 4507 - 4518 (2007/10/02)
Reactions and characterization of allylic and related zirconium reaegnts (allenic and γ-alkoxyallylic zirconiums) generated by treatment of allylic and/or propargylic ethers with a zirconocene-butene complex ("Cp2Zr") are described.
AgAsF6 as safe alternative to AgClO4 for generating cationic zirconocene species: Utilities in Lewis acid-promoted selective C---C bond forming reactions
Suzuki, Keisuke,Hasegawa, Takayuki,Imai, Takahiro,Maeta, Hideki,Ohba, Shigeru
, p. 4483 - 4494 (2007/10/02)
For generating cationic zirconocene species that are useful for organic synthesis, AgAsF6 proved to be an efficient catalyst that serves as a safe alternative to AgClO4. Scope and limitation is discussed on this new catalyst in the processes including (1) alkyl/alkenyl transfer reaction from organozirconocene chloride to aldehyde, (2) two- and four-carbon homologation of aldehyde, (3) dual synthetic methods of 1,3-dienes from aldehydes/ketones via 1,3-bimetallic species, and (4) three-component alkylative cycloaddition via o-quinodimethane species.
