151484-28-5Relevant articles and documents
Silver-Catalyzed Regioselective Phosphorylation of para-Quinone Methides with P(III)-Nucleophiles
Liu, Yu,Tang, Ke-Wen,Wong, Wai-Yeung,Xie, Jun,Xiong, Biquan,Xu, Shipan,Xu, Weifeng
, p. 14983 - 15003 (2021/11/12)
A simple and efficient method for the silver-catalyzed regioselective phosphorylation of para-quinone methides (p-QMs) with P(III)-nucleophiles (P(OR)3, ArP(OR)2, Ar2P-OR) has been established via Michaelis-Arbuzov-type reaction. A broad range of P(III)-nucleophiles and para-quinone methides are well tolerated under the mild conditions, giving the expected diarylmethyl-substituted organophosphorus compounds with good to excellent yields. Moreover, a series of corresponding enantiomers can be obtained by employing dialkyl arylphosphonite (ArP(OR)2) as substrates. The control experiments and 31P NMR tracking experiments were also performed to gain insights for the plausible reaction mechanism. This protocol may have significant implications for the formation of C(sp3)-P bonds in Michaelis-Arbuzov-type reactions.
Synthesis and characterisation of severely hindered P-OR compounds
Williams, D. Bradley G.,Netshiozwi, Takelani E.
experimental part, p. 9973 - 9982 (2010/02/27)
P-Cl substrates were converted into their P-OR analogues from hindered alcohols using an amine base. Where the system was severely hindered, more forcing conditions were required that necessitated the presence of a metal alkoxide nucleophile before succes
Efficient method for the preparation of inverted alkyl carboxylates and phenyl carboxylates via oxidation-reduction condensation using 2,6-dimethyl-1,4-benzoquinone or simple 1,4-benzoquinone
Shintou, Taichi,Fukumoto, Kentaro,Mukaiyama, Teruaki
, p. 1569 - 1579 (2007/10/03)
Oxidation-reduction condensation using in situ formed alkoxydiphenylphosphines, 2,6-dimethy-1,4-benzoquinone, and carboxylic acids provides a useful method for the preparation of inverted tertiary alkyl carboxylates from the corresponding chiral tertiary alcohols under mild and neutral conditions. Similarly, it has afforded alkyl carboxylates successfully in good-to-high yields by the combined use of alkoxydiphenylphosphines having primary, secondary, or tertiary alkoxy groups, carboxylic acids, and simple 1,4-benzoquinone. When chiral secondary or tertiary alcohols are used, the corresponding inverted secondary or tertiary alkyl carboxylates are also obtained in good-to-high yields. In addition, a convenient method for the preparation of phenyl carboxylates in high yields has been established by utilizing oxidation-reduction condensation in toluene at 110 °C using phenoxydiphenylphosphines in situ-formed from phenols and chlorodiphenylphosphine, 2,6-dimethyl-1,4-benzoquinone, and carboxylic acids.
Preparation of various carboxylic acid esters from bulky alcohols and carboxylic acids by a new type oxidation-reduction condensation using 2,6-dimethyl-1,4-benzoquinone
Mukaiyama, Teruaki,Kikuchi, Wataru,Shintou, Taichi
, p. 300 - 301 (2007/10/03)
A new-type oxidation-reduction condensation by using 2,6-dimethyl-1,4-benzoquinone (DMBQ), carboxylic acids and in situ formed alkoxydiphenylphosphines (1) including the bulky alkoxy group-substituted ones proceeded smoothly to afford the corresponding carboxylic acid esters in good to high yields. Alkoxydiphenylphosphines were formed in situ by treating either N,N-dimethylaminodiphenylphosphine (Ph2PNMe2) with primary or secondary alcohols or chlorodiphenylphosphine with the lithium salts of primary, secondary and tertiary alcohols.
Efficient Method for the Preparation of Primary, Inverted Secondary and Tertiary Alkyl Carboxylates from Alcohols and Carboxylic Acids by a New Type of Oxidation-Reduction Condensation Using Simple 1,4-Benzoquinone
Shintou, Taichi,Mukaiyama, Teruaki
, p. 1100 - 1101 (2007/10/03)
A new type of oxidation-reduction condensation using in situ formed alkoxydiphenylphosphines (i.e., diphenylphosphinite esters), easily available 1,4-benzoquionone and carboxylic acids provides a new and efficient method for the preparation of alkyl carboxylates from the corresponding alcohols under mild and neutral conditions. Further, the yields of the corresponding inverted carboxylates were equally high in the case of chiral secondary or tertiary alcohols.
Efficient method for the preparation of carboxylic acid alkyl esters or alkyl phenyl ethers by a new-type of oxidation-reduction condensation using 2,6-dimethyl-1,4-benzoquinone and alkoxydiphenylphosphines
Shintou, Taichi,Kikuchi, Wataru,Mukaiyama, Teruaki
, p. 1645 - 1667 (2007/10/03)
A new-type of oxidation-reduction condensation proceeded smoothly to afford carboxylic acid alkyl esters or alkyl phenyl ethers in good to high yields by combined use of alkoxydiphenylphosphines (1) having primary, bulky secondary or tertiary alkoxy groups, a mild quinone-type oxidant such as 2,6-dimethyl-1,4-benzoquinone (DMBQ) and carboxylic acids or phenols. Generally, alkoxydiphenylphosphines were prepared easily from chlorodiphenylphosphine (2) and alcohols in the presence of pyridine, and were isolated by distillation. On the other hand, the phosphines 1 were also prepared in situ from N,N-dimethylaminodiphenylphosphine (3a) and primary or secondary alcohols while primary, bulky secondary or tertiary alkoxydiphenylphosphines were alternatively formed in situ by adding 2 to the "BuLi-treated alcohols in order to perform the above reactions by a one-pot procedure from alcohols and nucleophiles. The reaction of thus formed 1, DMBQ and carboxylic acids or phenols afforded the corresponding alkylated products, including hindered secondary and tertiary alkylated ones, in good to high yields at room temperature. In the case of using chiral secondary alcohols, the corresponding carboxylic acid alkyl esters were obtained as well in high yields with perfect inversion of stereochemistry by SN2 replacement.
Structural studies of PdCl2L2 complexes with fluorinated phosphines, phosphites, and phosphinites as precursors of benzyl bromide carbonylation catalysts, and and X-ray crystal structure of cis-PdCl2[PPh2 (OEt)]2
Trzeciak,Bartosz-Bechowski,Ciunik,Niesyty,Ziolkowski
, p. 752 - 759 (2007/10/03)
PdCl2L2-type complexes with phosphines (L = PPhx(C6F5)3-x (x = 0-3)), phosphites (L = P(OMe)3, P(OPh)3, P(OEt)3), and phosphinites (L = PPh2 (OC6F5), PPh2(O-3,5-F2 C6H3), PPh2(OEt), PPh2 (O-n-Bu), PPh2(O-t-Bu)) were synthesized and characterized by UV-vis and 31P NMR methods. PdCl2L2 complexes with less sterically demanding phosphines (Θ 2[PPh2(OEt)]2. These complexes react with CO in the presence of NEt3 forming Pd(CO)xLy (x + y = 4) type carbonyls characterized by IR spectra. All PdCl2L2 complexes studied are active as precursors of benzyl bromide carbonylation catalysts at 40°C and 1 atm CO; however, the activity of the cis isomers is higher than that of the trans isomers. The highest yields of the carbonylation product, phenylacetic acid methyl ester, were obtained using cis-PdCl2[P(OMe)3]2 (92%), cis-PdCl2[P(OPh)3]2 (89%), and cis-PdCl2[PPh2(O-n-Bu)]2 (78%) as catalyst precursors.
