Synthesis of functionalized salicylate esters and amides by photochemical acylation

Omid Soltani, Jef K. De Brabander

Research output: Contribution to journalArticle

35 Citations (Scopus)

Abstract

(Chemical Equation Presented) Functionalized salicylates in a flash: Photolysis of functionalized benzodioxinones in the presence of alcohols or amines is a powerful method for the synthesis of sterically hindered salicylic esters and amides (see scheme). This reaction tolerates a broad range of functional groups and efficiently engages a wide range of acylation substrates, including sterically hindered nucleophiles that are inert to other acylation methods.

Original languageEnglish (US)
Pages (from-to)1696-1699
Number of pages4
JournalAngewandte Chemie - International Edition
Volume44
Issue number11
DOIs
StatePublished - Mar 4 2005

Fingerprint

Acylation
Salicylates
Amides
Esters
Nucleophiles
Photolysis
Functional groups
Amines
Alcohols
Substrates

Keywords

  • Acylation
  • Natural products
  • Photochemistry
  • Synthetic methods

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Synthesis of functionalized salicylate esters and amides by photochemical acylation. / Soltani, Omid; De Brabander, Jef K.

In: Angewandte Chemie - International Edition, Vol. 44, No. 11, 04.03.2005, p. 1696-1699.

Research output: Contribution to journalArticle

@article{269ad09f65964cbcb410a9be30ed8d3b,
title = "Synthesis of functionalized salicylate esters and amides by photochemical acylation",
abstract = "(Chemical Equation Presented) Functionalized salicylates in a flash: Photolysis of functionalized benzodioxinones in the presence of alcohols or amines is a powerful method for the synthesis of sterically hindered salicylic esters and amides (see scheme). This reaction tolerates a broad range of functional groups and efficiently engages a wide range of acylation substrates, including sterically hindered nucleophiles that are inert to other acylation methods.",
keywords = "Acylation, Natural products, Photochemistry, Synthetic methods",
author = "Omid Soltani and {De Brabander}, {Jef K.}",
year = "2005",
month = "3",
day = "4",
doi = "10.1002/anie.200462577",
language = "English (US)",
volume = "44",
pages = "1696--1699",
journal = "Angewandte Chemie - International Edition",
issn = "1433-7851",
publisher = "John Wiley and Sons Ltd",
number = "11",

}

TY - JOUR

T1 - Synthesis of functionalized salicylate esters and amides by photochemical acylation

AU - Soltani, Omid

AU - De Brabander, Jef K.

PY - 2005/3/4

Y1 - 2005/3/4

N2 - (Chemical Equation Presented) Functionalized salicylates in a flash: Photolysis of functionalized benzodioxinones in the presence of alcohols or amines is a powerful method for the synthesis of sterically hindered salicylic esters and amides (see scheme). This reaction tolerates a broad range of functional groups and efficiently engages a wide range of acylation substrates, including sterically hindered nucleophiles that are inert to other acylation methods.

AB - (Chemical Equation Presented) Functionalized salicylates in a flash: Photolysis of functionalized benzodioxinones in the presence of alcohols or amines is a powerful method for the synthesis of sterically hindered salicylic esters and amides (see scheme). This reaction tolerates a broad range of functional groups and efficiently engages a wide range of acylation substrates, including sterically hindered nucleophiles that are inert to other acylation methods.

KW - Acylation

KW - Natural products

KW - Photochemistry

KW - Synthetic methods

UR - http://www.scopus.com/inward/record.url?scp=17044384198&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=17044384198&partnerID=8YFLogxK

U2 - 10.1002/anie.200462577

DO - 10.1002/anie.200462577

M3 - Article

VL - 44

SP - 1696

EP - 1699

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 11

ER -