33603-89-3Relevant academic research and scientific papers
Modular Synthesis of α-Substituted Alkenyl Acetals by a Palladium-Catalyzed Suzuki Reaction of α-Haloalkenyl Acetals with Organoboranes
Zhang, Li
, p. 723 - 727 (2021/02/26)
A modular and straightforward synthetic strategy for the preparation of α-substituted alkenyl acetals has been developed. α-Haloalkenyl acetals react smoothly with (het)aryl boronic acids, aryl boronates, or B-Alkyl-9-borabicyclo[3.3.1]nonanes through Pd-catalyzed Suzuki cross-coupling under mild conditions with good to high yields. This protocol features a broad substrate scope and good functional-group compatibility, and is easily scaled up.
The α-halogenation of α,β-unsaturated carbonyls and dihalogenation of alkenes using bisacetoxyiodobenzene/pyridine hydrohalides
Ngatimin, Marsewi,Gartshore, Christopher J.,Kindler, Jeremy P.,Naidu, Sudha,Lupton, David W.
experimental part, p. 6008 - 6011 (2010/03/03)
A procedure for the α-chlorination or bromination of a number of α,β-unsaturated carbonyls, and the dichlorination or bromination of alkenes, is developed using bisacetoxyiodobenzene (BAIB) and the HCl or HBr salt of pyridine. The reaction proceeds in an
Convenient preparation of (Z)-α-halo-α,β-unsaturated aldehydes: synthesis of a Laurencia flexilis toxin
Barma, Deb K.,Lu, Biao,Baati, Rachid,Mioskowski, Charles,Falck
, p. 4359 - 4361 (2008/12/21)
The CrCl2-mediated two-carbon halo-homologation of aryl, alkenyl, and aliphatic aldehydes with chloral ethyl hemiacetal or bromal affords (Z)-α-chloro- and (Z)-α-bromo-α,β-unsaturated aldehydes, respectively, in good to excellent yields and high stereoselectivity. The utility of this methodology was illustrated by a synthesis of 2-chloropentadec-2(Z)-enal, a toxin isolated from the marine red alga Laurencia flexilis.
α-Bromination of linear enals and cyclic enones
Bovonsombat, Pakorn,Rujiwarangkul, Rungkarn,Bowornkiengkai, Thanathip,Leykajarakul, Juthamard
, p. 8607 - 8610 (2008/03/30)
Facile α-bromination of cyclic enones and linear enals involving N-bromosuccinimide and 1-2 equiv of pyridine-N-oxide is reported herein. α-Bromination of linear enals was found to proceed with double bond geometry retention.
A convenient halogenation of α,β-unsaturated carbonyl compounds with OXONE and hydrohalic acid (HBr,HCl)
Kim, Kyoung-Mahn,Park, In-Hwan
, p. 2641 - 2644 (2007/10/03)
Mixtures of OXONE and hydrobromic acid or hydrochloric acid afford solutions of bromine or chlorine, respectively, α-Bromo- or α-chloro-α,β-unsaturated carbonyl compounds were prepared by addition of hydrobromic acid or hydrochloric acid to the mixture of
Ligand exchange reaction of sulfoxides in organic synthesis: A novel method for generation of magnesium enolates and its application to synthesis of α-halocarboxylic acid derivatives and α-haloaldehydes
Satoh,Kitoh,Onda,Takano,Yamakawa
, p. 4957 - 4972 (2007/10/02)
A new method for synthesis of α-halo(Cl, F)carboxylic acid derivatives and α-haloaldehydes is described. α-Halo-α-sulfinyl carboxylic acid, esters, and α-halo-α-sulfinyl aldehydes were easily prepared from aryl 1-haloalkyl sulfoxides and alkyl chloroformate and ethyl formate, respectively, in good yields. α-Chloro-α-sulfinyl amides were synthesized from (p-tolylthio)acetic acid. Ligand exchange reaction of the sulfinyl group of these acids, esters, amides, and aldehydes with ethylmagnesium bromide gave the magnesium enolates, which were treated with water to give α-halocarboxylic acid derivatives and α-chloroaldehydes in good yields. The magnesium enolates derived from the α-chloro-α-sulfinyl acid derivatives were trapped with carbonyl compounds to afford the adducts, which were transformed to α,β-epoxy carboxylic acid derivatives. Thermal elimination of the sulfinyl group in the α-halo-α-sulfinyl acid derivatives and the α-halo-sulfinyl aldehydes gave α-halo-α,β-unsaturated carboxylic acid derivatives and α-halo-α,β-unsaturated aldehydes in high yields.
Formation of 2-phenylselenenylenones and 2-haloenones from enones. Mechanistic and synthetic aspects, X-ray crystal structures of intermediates
Engman, Lars,Toernroos, Karl Wilhelm
, p. 165 - 178 (2007/10/02)
The structure of trans-3-chloro-2-phenylselenenylcyclohexanone (1) was determined by X-ray diffraction.Although this and similar compounds were readily dehydrohalogenated to give vinylic selenides, they were ruled out as intermediates in the synthesis of
Reaction of Benzeneseleninyl Chloride with Olefins in the Presence of a Lewis Acid. A Novel One Step Vinylic Chlorination
Kamigata, Nobumasa,Satoh, Takeshi,Yoshida, Masato
, p. 449 - 454 (2007/10/02)
In the presence of aluminum chloride benzeneseleninyl chloride was found to be an exellent vinylic chlorinating reagent of olefins under mild conditions.However, such olefins as styrene, trans-stilbene, and trans-1-phenylpropene afforded dichloro adducts under similar conditions.A plausible reaction mechanism involving positive chlorine intermediate is proposed.
