133678-75-8

Upstream product

• 88738-78-7 bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 623-43-8 crotonic acid methyl ester 
• 98-68-0 4-methoxy-phenyl-sulphonyl chloride 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 99142-77-5 methyl (E)-3-(3-methoxyphenyl)-3-methylacrylate 
• 105-45-3 acetoacetic acid methyl ester 
• 1029612-18-7 (Z)-methyl 3-(p-toluenesulfonyloxy)but-2-enoate 
• 93296-09-4 4-methoxyphenylzinc chloride 
• 623-43-8 methyl crotonate 
• 696-62-8 para-iodoanisole 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 1067-74-9 Methyl diethylphosphonoacetate 

Relevant academic research and scientific papers

Heteroleptic Copper-Based Complexes for Energy-Transfer Processes: E → Z Isomerization and Tandem Photocatalytic Sequences

Energy-transfer processes involving copper complexes are rare. Using an optimized heteroleptic copper complex, Cu(bphen)(XantPhos)BF4, photosensitized E → Z isomerization of olefins is demonstrated. The XantPhos ligand afforded sensitizers with improved catalyst stability, while the bphen ligand lengthened the excited-state lifetime. A series of 25 di- and trisubstituted alkenes underwent photoisomerization, including macrocycles and 1,3-enynes. Cu(bphen)(XantPhos)BF4 could also be employed in a tandem ATRA/photoisomerization process employing arylsulfonyl chlorides, an example of photoisomerization with halide-substituted olefins.

Microwave-Assisted Synthesis of Phenylpropanoids and Coumarins: Total Synthesis of Osthol

Herein we describe a one-pot microwave-assisted method for the synthesis of cinnamic acid and coumarin derivatives. The synthesis begins with an aldehyde synthon, and the chosen reaction conditions determine whether a cinnamic acid or coumarin derivative is formed. A regioselective Claisen rearrangement was also efficiently incorporated into the synthetic sequence to further increase the complexity of the product. Notably, this approach provides high product yields and selectivities without the need of a phenol protecting group.

Pd-arylurea complexes for the Heck arylation of crotonic and cinnamic substrates

A catalyst consisting of the 1:2 complex of Pd(OAc)2 (1 mol %) with N-(4-carbethoxy)-phenylurea promotes the Heck arylation of a range of crotonic and cinnamic substrates, including aldehydes, ketones, esters, and nitriles, with electron-rich - but not electron-deficient - aryl iodides.

General, robust, and stereocomplementary preparation of β-ketoester enol tosylates as cross-coupling partners utilizing TsCl-N-methylimidazole agents

(Chemical Equation Presented) We have developed a general, robust, and cost-effective method for the (E)- or (Z)-stereocomplementary enol tosylation of β-ketoesters using TsCl-N-methylimidazole (NMI)-Et3N or LiOH. TsCl coupled with NMI formed a

Palladium-catalyzed desulfitative mizoroki-heck couplings of sulfonyl chlorides with mono-and disubstituted olefins: Rhodium-catalyzed desulfitative heck-type reactions under phosphine- And base-free conditions

New conditions have been found for the desulfitative Mizoroki-Heck arylation and trifluoromethylation of mono- and disubustituted olefins with arenesulfonyl and trifluoro-methanesulfonyl chlorides. Thus (E)-1,2- disubstituted alkenes with high ster-eoselectivity and 1,1,2-disubstituted alkenes with 12:1 to 21:1 E/Z steroselectivity can be obtained. Herrmann's palladacycle at 0.1 mol% is sufficient to catalyze these reactions, for which electron-rich or electron-poor sulfonyl chlorides and alkenes are suitable. If phosphine- and base-free conditions are required. 1 mol% [RriCl(C 2,H4)2] catalyzes the desulfitative cross-cou pling reactions. Contrary to results reported for [RuCl2(PPh 3)2]-catalyzed coupling reactions with sulfonyl chlorides, the palladium and rhodium desulfitative Mizoroki-Heck coupling reactions are not inhibited by radical scavenging agents. Possible sulfones arising from the sulfonylation of alkenes at 60°C are not desulfitated at higher temperatures in the presence of the Pd or Rh catalysts.

A facile method for the stereoselective Horner-Wadsworth-Emmons reaction of aryl alkyl ketones.

Excellent Z or E selectivity was observed in the Horner-Wadsworth-Emmons (HWE) reactions of methyl bis(2,2,2-trifluoroethyl)phosphonoacetate or ethyl 2-fluoro-2-diethylphosphonoacetate with aryl alkyl ketones bearing substituents on an aromatic moiety employing Sn(OSO2CF3)2 in the presence of N-ethylpiperidine.

Remarkable reversal of stereoselectivity in Wittig-type olefinations of α-fluorinated alkyl aryl ketones

Remarkable reactivity and reversal of stereoselectivity in the Wittig-type olefinations of α-fluorinated alkyl aryl ketones were described. Stabilized Wittig and Horner-Emmons reagents with these ketones selectively afforded the olefinic products in the stereochemically opposite fashion to the non-fluorinated ketone cases. The Still's reagent further reversed the stereochemical outcome with the fluorinated ketones.

(Z)‐enol p‐tosylate derived from methyl acetoacetate: A useful cross‐coupling partner for the synthesis of methyl (Z)‐3‐phenyl (or aryl)‐2‐butenoate

Procedures yielding (Z)‐3‐(p‐toluenesulfonyloxy)but‐2‐enoate [(Z)‐1] as white prisms and methyl (Z)‐3‐phenyl‐2‐butenoate [(Z)‐2] as a colorless oil are presented. Following are notes on the instruments and chemicals used and required. The chapter conclude