73505-47-2Relevant academic research and scientific papers
Radical-Mediated Heck-Type Alkylation: Stereoconvergent Synthesis of Functionalized Polyenes
Zhang, Hong,Wu, Xinxin,Wei, Yunlong,Zhu, Chen
supporting information, p. 7568 - 7572 (2019/10/02)
The stereospecific synthesis of polyenes is of great synthetic value. Disclosed herein is a new, efficient, stereoconvergent approach for the synthesis of functionalized polyenes via a radical-mediated Heck-type alkylation. The easily accessed Z- and E-mixed alkenes are harnessed as starting material, leading to a unique stereoisomer of polyenes. In addition, the transformation features mild reaction conditions and broad functional group compatibility. A variety of valuable 1,3-dienes and 1,3,5-trienes are afforded in useful yields.
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.).
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.
Subsituted 4-(2-alkenylsulfinyl)morpholines : preparation and conversion into the corresponding sulfinic acids and esters. Stereochemistry of olefin formation by hydrolytic desulfinylation of allylic sulfinamides.
Baudin, Jean-Bernard,Julia, Sylvestre
, p. 196 - 214 (2007/10/02)
By reaction with 4-(chlorosulfenyl)morpholine in the presence of triethylamine, several substituted allylic alcohols have been converted into the title sulfinamides.As a complementary method, the new α-lithio allylic sulfinamides have been prepared and efficiently alkylated with organic halides.The boron trifluoride-etherate catalyzed treatment of the allylic sulfinamides with simple saturated alcohols provided the corresponding alkyl sulfinates while propargylic and allylic alcohols opened a route to various α,α'-bis-unsaturated sulfones.Efficient conditions for the acid-catalyzed hydrolysis of allylic sulfinamides are described and some allylic sulfinic acids bearing an electron-withdrawing group were isolated.Smooth fragmentation of the homoconjugated sulfinic acids gave the corresponding (E)-olefins stereoselectively. - Key words: sigmatropic rearrangement / allylic sulfinamide / allylic sulfinic ester / organolithium derivative / sulfone / retro-ene reaction / sulfur dioxide elimination / stereochemistry
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.
