Convenient synthesis of α-diarylmethylphosphonates by HOTf catalyzed Friedel-Crafts arylation of α-aryl α-hydroxyphosphonates

Chen, Long; Zou, Yun‐Xiang; Fang, Xinyue; Xu, Yin

doi:10.1080/10426507.2017.1393424

Cited by 5 publications

(2 citation statements)

References 21 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The Friedel-Crafts alkylation using α-hydroxyphosphonates 1 in the presence of an acid catalyst (e.g., FeCl 3 or HOTf) led to α,α-diarylphosphonates 53 [ 132 , 133 , 134 ]. Benzene and naphthalene served as the aromatic substrate.…”

Section: Reactions Of α-Hydroxyphosphonatesmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis and Reactions of α-Hydroxyphosphonates

Rádai

Keglevich

2018

Molecules

View full text Add to dashboard Cite

This review summarizes the main synthetic routes towards α-hydroxyphosphonates that are known as enzyme inhibitors, herbicides and antioxidants, moreover, a number of representatives express antibacterial or antifungal effect. Special attention is devoted to green chemical aspects. α-Hydroxyphosphonates are also versatile intermediates for other valuable derivatives. O-Alkylation and O-acylation are typical reactions to afford α-alkoxy-, or α-acyloxyphosphonates, respectively. The oxidation of hydroxyphosphonates leads to ketophosphonates. The hydroxy function at the α carbon atom of hydroxyphosphonates may be replaced by a halogen atom. α-Aminophosphonates formed in the nucleophilic substitution reaction of α-hydroxyphosphonates with primary or secondary amines are also potentially bioactive compounds. Another typical reaction is the base-catalyzed rearrangement of α-hydroxy-phosphonates to phosphates. Hydrolysis of the ester function of hydroxyphosphonates leads to the corresponding phosphonic acids.

show abstract

Section: Reactions Of α-Hydroxyphosphonatesmentioning

confidence: 99%

“…Benzene and naphthalene served as the aromatic substrate. According to the proposed mechanism, the first step is the formation of benzylphosphonate carbocation 52 that is followed by its electrophilic attack on the aromatic substrate ( Scheme 26 ) [ 132 ].…”

Section: Reactions Of α-Hydroxyphosphonatesmentioning

confidence: 99%

Synthesis and Reactions of α-Hydroxyphosphonates

Rádai

Keglevich

2018

Molecules

View full text Add to dashboard Cite

show abstract

A highly efficient nucleophilic substitution reaction between R₂P(O)H and triarylmethanols to synthesize phosphorus-substituted triarylmethanes

2018

View full text Add to dashboard Cite

A highly efficient and general nucleophilic substitution reaction between dialkyl H-phosphonates or diarylphosphine oxides and triarylmethanols catalyzed by HOTf (trifluoromethanesulfonic acid) has been developed. It provides an atom-economical protocol for the synthesis of various symmetrical and unsymmetrical phosphorus-substituted triarylmethanes that constitute an emerging family of potent anticancer agents in rich diversity with 40 to 96% yields. The synthetic applicability of this protocol is demonstrated by gram-scale preparations.

show abstract

Brønsted acid-catalysed regiodivergent phosphorylation of 2-indolylmethanols to synthesize benzylic site or C3-phosphorylated indole derivatives

et al. 2018

View full text Add to dashboard Cite

A Brønsted acid catalysed regiodivergent phosphorylation of 2-indolylmethanols with diarylphosphine oxides has been established, which provides a brand-new strategy for accessing highly functionalized phosphorus-containing indoles with structural diversity. Under the catalysis of HOTs·H2O, 2-indolylmethanols undergo regioselective benzylic phosphorylation at room temperature to afford benzylic site phosphorylated indoles in good to high yields (29 examples, up to 98% yield), while C3-phosphorylated indoles are obtained in the presence of HOTf under heating conditions (16 examples, up to 83% yield). Preliminary mechanistic studies suggest that C3-phosphorylated indoles are possibly obtained partially from direct C3-phosphorylation and dominantly from a tandem benzylic phosphorylation/[1,3]-P migration/isomerization sequence from 2-indolylmethanols. Furthermore, the acidity of the Brønsted acid and the reaction temperature play a vital role in the [1,3]-P migration of benzylic phosphorylated indoles to form C3-phosphorylated indoles. This protocol serves as a good example for regioselective benzylic functionalization of 2-indolylmethanols.

show abstract

Convenient synthesis of α-diarylmethylphosphonates by HOTf catalyzed Friedel-Crafts arylation of α-aryl α-hydroxyphosphonates

Cited by 5 publications

References 21 publications

Synthesis and Reactions of α-Hydroxyphosphonates

Synthesis and Reactions of α-Hydroxyphosphonates

A highly efficient nucleophilic substitution reaction between R₂P(O)H and triarylmethanols to synthesize phosphorus-substituted triarylmethanes

Brønsted acid-catalysed regiodivergent phosphorylation of 2-indolylmethanols to synthesize benzylic site or C3-phosphorylated indole derivatives

Contact Info

Product

Resources

About

Convenient synthesis of α-diarylmethylphosphonates by HOTf catalyzed Friedel-Crafts arylation of α-aryl α-hydroxyphosphonates

Cited by 5 publications

References 21 publications

Synthesis and Reactions of α-Hydroxyphosphonates

Synthesis and Reactions of α-Hydroxyphosphonates

A highly efficient nucleophilic substitution reaction between R2P(O)H and triarylmethanols to synthesize phosphorus-substituted triarylmethanes

Brønsted acid-catalysed regiodivergent phosphorylation of 2-indolylmethanols to synthesize benzylic site or C3-phosphorylated indole derivatives

Contact Info

Product

Resources

About

A highly efficient nucleophilic substitution reaction between R₂P(O)H and triarylmethanols to synthesize phosphorus-substituted triarylmethanes