The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 4-Methyl-1-phenyl-2,3-dihydro-1H-phosphole 1-oxide( cas:707-61-9 ) is researched.Product Details of 707-61-9.O’Brien, Christopher J.; Nixon, Zachary S.; Holohan, Andrew J.; Kunkel, Stephen R.; Tellez, Jennifer L.; Doonan, Bryan J.; Coyle, Emma E.; Lavigne, Florie; Kang, Lauren J.; Przeworski, Katherine C. published the article 《Part I: The Development of the Catalytic Wittig Reaction》 about this compound( cas:707-61-9 ) in Chemistry – A European Journal. Keywords: Wittig reaction phosphole phospholane phosphate oxide preparation catalyst; Wittig reaction; alkenes; homogeneous catalysis; olefination; organocatalysis. Let’s learn more about this compound (cas:707-61-9).
The authors have developed the first catalytic (in phosphane) Wittig reaction (CWR). The utilization of an organosilane was pivotal for success as it allowed for the chemoselective reduction of a phosphane oxide. Protocol optimization evaluated the phosphane oxide pre-catalyst structure, loading, organosilane, temperature, solvent, and base. These studies demonstrated that to maintain viable catalytic performance it was necessary to employ cyclic phosphane oxide pre-catalysts of type 1. Initial substrate studies utilized sodium carbonate as a base, and further experimentation identified N,N-diisopropylethylamine (DIPEA) as a soluble alternative. The use of DIPEA improved the ease of use, broadened the substrate scope and decreased the pre-catalyst loading. The optimized protocols were compatible with alkyl, aryl, and heterocyclic (furyl, indolyl, pyridyl, pyrrolyl, and thienyl) aldehydes to produce both disubstituted and trisubstituted olefins in moderate-to-high yields (60-96%) by using a pre-catalyst loading of 4-10 mol%. Kinetic E/Z selectivity was generally 66:34. Complete (E)-selectivity for disubstituted α,β-unsaturated products was achieved through a phosphane-mediated isomerization event. The CWR was applied to the synthesis of a known precursor to the anti-Alzheimer drug donepezil hydrochloride, on a multi-gram scale (12.2 g, 74% yield). In addition, the described CWR is the only transition-metal-free/heavy-metal-free catalytic olefination process, excluding proton-catalyzed elimination reactions. The synthesis of the target compounds was achieved (1R,3S)-rel-3-methyl-1-phenylphospholane 1-oxide, (1R,3R)-rel-3-methyl-1-phenylphospholane 1-oxide, 1-phenylphospholane 1-oxide as catalyst precursors. 2-Phenyl-1,3,2-dioxaphospholane 2-oxide, diethylphenylphosphine oxide, 5-phenyl-5H-benzo[b]phosphindole 5-oxide, (2R,2’R,5R,5’R)-1,1′-(1,2-ethanediyl)bis[2,5-bis(1-methylethyl)phospholane], 2-[2-[(2R,5R)-2,5-dimethyl-1-phospholanyl]phenyl]-1,3-dioxolane were also evaluated.
Compounds in my other articles are similar to this one(4-Methyl-1-phenyl-2,3-dihydro-1H-phosphole 1-oxide)Product Details of 707-61-9, you can compare them to see their pros and cons in some ways,such as convenient, effective and so on.
Reference:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem