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Route to α-Aryl Phosphonoacetates: Useful Synthetic Precursors in the Horner-Wadsworth-Emmons Olefination.

VanGelder KF, Wang M, Kozlowski MC - J. Org. Chem. (2015)

Bottom Line: These α-substituted phosphonoacetates are widely useful, notably as substrates in the Horner-Wadsworth-Emmons-type olefinations.However, the current routes to these products involve harsh conditions, limiting the variety of functionality.The reported method can be used with a variety of aryl chlorides and aryl bromides, including several heterocyclic examples.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, Roy and Diana Vagelos Laboratories, University of Pennsylvania , Philadelphia, Pennsylvania 19104-6323, United States.

ABSTRACT
A versatile and general catalytic strategy has been developed for the α-arylation of phosphonoacetates utilizing parallel microscale experimentation. These α-substituted phosphonoacetates are widely useful, notably as substrates in the Horner-Wadsworth-Emmons-type olefinations. However, the current routes to these products involve harsh conditions, limiting the variety of functionality. The reported method can be used with a variety of aryl chlorides and aryl bromides, including several heterocyclic examples.

No MeSH data available.


Substrate Scope of the α-Arylation of TriethylPhosphonoacetatewith Aryl ChloridesReactions were conducted at 100°C in CPME, with 1.25 mol % of Pd2(dba)3, 5 mol % of BrettPhos, 1.2 equiv of Cs2CO3, and 1.1 equiv of aryl chloride.Reactions were conducted at 100 °C in CPME, with 2.5 mol %of Pd2(dba)3, 10 mol % of BrettPhos, 1.2 equivof Cs2CO3, and 1.1 equiv of aryl chloride.
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sch5: Substrate Scope of the α-Arylation of TriethylPhosphonoacetatewith Aryl ChloridesReactions were conducted at 100°C in CPME, with 1.25 mol % of Pd2(dba)3, 5 mol % of BrettPhos, 1.2 equiv of Cs2CO3, and 1.1 equiv of aryl chloride.Reactions were conducted at 100 °C in CPME, with 2.5 mol %of Pd2(dba)3, 10 mol % of BrettPhos, 1.2 equivof Cs2CO3, and 1.1 equiv of aryl chloride.


Route to α-Aryl Phosphonoacetates: Useful Synthetic Precursors in the Horner-Wadsworth-Emmons Olefination.

VanGelder KF, Wang M, Kozlowski MC - J. Org. Chem. (2015)

Substrate Scope of the α-Arylation of TriethylPhosphonoacetatewith Aryl ChloridesReactions were conducted at 100°C in CPME, with 1.25 mol % of Pd2(dba)3, 5 mol % of BrettPhos, 1.2 equiv of Cs2CO3, and 1.1 equiv of aryl chloride.Reactions were conducted at 100 °C in CPME, with 2.5 mol %of Pd2(dba)3, 10 mol % of BrettPhos, 1.2 equivof Cs2CO3, and 1.1 equiv of aryl chloride.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4612770&req=5

sch5: Substrate Scope of the α-Arylation of TriethylPhosphonoacetatewith Aryl ChloridesReactions were conducted at 100°C in CPME, with 1.25 mol % of Pd2(dba)3, 5 mol % of BrettPhos, 1.2 equiv of Cs2CO3, and 1.1 equiv of aryl chloride.Reactions were conducted at 100 °C in CPME, with 2.5 mol %of Pd2(dba)3, 10 mol % of BrettPhos, 1.2 equivof Cs2CO3, and 1.1 equiv of aryl chloride.
Bottom Line: These α-substituted phosphonoacetates are widely useful, notably as substrates in the Horner-Wadsworth-Emmons-type olefinations.However, the current routes to these products involve harsh conditions, limiting the variety of functionality.The reported method can be used with a variety of aryl chlorides and aryl bromides, including several heterocyclic examples.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry, Roy and Diana Vagelos Laboratories, University of Pennsylvania , Philadelphia, Pennsylvania 19104-6323, United States.

ABSTRACT
A versatile and general catalytic strategy has been developed for the α-arylation of phosphonoacetates utilizing parallel microscale experimentation. These α-substituted phosphonoacetates are widely useful, notably as substrates in the Horner-Wadsworth-Emmons-type olefinations. However, the current routes to these products involve harsh conditions, limiting the variety of functionality. The reported method can be used with a variety of aryl chlorides and aryl bromides, including several heterocyclic examples.

No MeSH data available.