77525-89-4

Upstream product

• 117024-23-4 (η(5)-C5H5)(CO)2Fe-CH(OMe)(p-OCH3Ph) 
• 25679-28-1 cis-Anethole 
• 75-09-2 dichloromethane 
• 4180-23-8 E-1-(4'-methoxyphenyl)prop-1-ene 
• 123-11-5 4-methoxy-benzaldehyde 
• 114095-59-9 (1S*, 2S*)-2-((4-methoxyphenyl)cyclopropyl)methanol 
• 110826-20-5 (±)-trans-2-(4-methoxyphenyl)cyclopropanecarboxylic acid 
• 104-46-1 anethole 
• 75-11-6 diiodomethane 
• 243665-13-6 (2E)-N-methoxy-3-(4-methoxyphenyl)-N-methylprop-2-enamide 

Downstream Products

• 142746-00-7 3-methyl-5-(4-methoxyphenyl)-2-isoxazoline 
• 142746-12-1 4-methyl-5-(4-methoxyphenyl)-2-isoxazoline 

Relevant academic research and scientific papers

Redox-Neutral Photocatalytic Cyclopropanation via Radical/Polar Crossover

A benchtop stable, bifunctional reagent for the redox-neutral cyclopropanation of olefins has been developed. Triethylammonium bis(catecholato)iodomethylsilicate can be readily prepared on multigram scale. Using this reagent in combination with an organic photocatalyst and visible light, cyclopropanation of an array of olefins, including trifluoromethyl- and pinacolatoboryl-substituted alkenes, can be accomplished in a matter of hours. The reaction is highly tolerant of traditionally reactive functional groups (carboxylic acids, basic heterocycles, alkyl halides, etc.) and permits the chemoselective cyclopropanation of polyolefinated compounds. Mechanistic interrogation revealed that the reaction proceeds via a rapid anionic 3-exo-tet ring closure, a pathway consistent with experimental and computational data.

A Stereoconvergent Cyclopropanation Reaction of Styrenes

The first stereoconvergent cyclopropanation reaction by means of photoredox catalysis using diiodomethane as the methylene source is described. This transformation exhibits broad functional group tolerance and it is characterized by an excellent stereocontrol en route to trans-cyclopropanes regardless of whether E- or Z-styrene substrates were utilized.

Reductive Cyclopropanations Catalyzed by Dinuclear Nickel Complexes

Dinuclear Ni complexes supported by naphthyridine-diimine (NDI) ligands catalyze the reductive cyclopropanation of alkenes with CH2Cl2 as the methylene source. The use of mild terminal reductants (Zn or Et2Zn) confers significant functional-group tolerance, and the catalyst accommodates structurally and electronically diverse alkenes. Mononickel catalysts bearing related N chelates afford comparatively low cyclopropane yields (≤20 %). These results constitute an entry into catalytic carbene transformations from oxidized methylene precursors.

Highly diastereoselective hydrostannylation of allyl and homoallyl alcohols with dibutyl(trifluoromethanesulfoxy)stannane

Dibutyl(trifluoromethanesulfoxy)stannane (Bu2Sn(OTf)H, 1a) was found to be very valuable for highly diastereoselective homolytic hydrostannylation of allyl and homoallyl alcohols. α,β-Disubstituted allyl alcohols and α,γ-disubstituted homoallyl alcohols were converted into γ- and δ-stannylated alcohols with high 1,2-syn and 1,3-syn diastereoselectivity, respectively. The origin of the stereochemical outcomes can be rationalized by conformational fixation of the intermediary β-stannylalkyl radical by coordination of the hydroxy group to the Lewis acidic tin center. Copyright

Picosecond radical kinetics. Rate constants for ring openings of 2-aryl-substituted cyclopropylcarbinyl radicals

The kinetics of ring openings of a series of eight (trans-2-arylcyclopropyl)methyl radicals (1) were studied by indirect kinetic methods using Barton's PTOC esters as radical precursors and reaction with PhSeH as the competition reaction. The substituents were CF3, F, Me, and OMe located on both the para and meta positions of the aromatic ring. Syntheses of the radical precursors and the products of the radical reactions are described. Kinetics were determined between -43 and 25°C in four cases (CF3 and OMe substituents) and at 0 and 25°C in the other four cases. The rate constants at 25°C ranged from 1.0 x 1011 s-1 (p-CH3) to 4.1 x 1011 s-1 (p-CF3). The relatively large acceleration of the p-CF3 group, ca. 2.5 times as fast as the parent system with Ar = Ph, correlates well with Adam's ΔD substituent parameters but not with other radical substituent parameters. These calibrated radical rearrangements provide a new set of ultrafast reactions that can be applied in mechanistic probe studies.

Synthesis and spectral characterization of a series of iron and ruthenium benzylidene complexes, Cp(CO)(L)M=CH(C6H4R)+ (M = Fe, Ru; L = CO, PPh3; R = p-H, p-F, p-CH3, p-OCH3). Barriers to a

The α-ether complexes Cp(CO)2Fe-CH(OCH3)C6H4R (7a, R = H; 7b, R = p-F; 7c, R = p-CH3; 7d, R = p-OCH3; 7e, R = m-OCH3; 7f, R = p-CF3), Cp(CO)2Ru-CH(OCH3