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Regioselective aerobic oxidative Heck reactions with electronically unbiased alkenes: efficient access to α-alkyl vinylarenes.

Branched-selective oxidative Heck coupling reactions have been developed between arylboronic acids and electronically unbiased terminal alkenes. The reactions exhibit high catalyst-controlled regioselectivity favoring the less common branched isomer. The reactions employ a catalyst composed of Pd(TF... Full description

Journal Title: Chemical communications (Cambridge England), August 18, 2015, Vol.51(64), pp.12771-12774
Main Author: Zheng, Changwu
Other Authors: Stahl, Shannon S
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: E-ISSN: 1364-548X ; DOI: 1364-548X ; DOI: 10.1039/c5cc05312a
Link: http://search.proquest.com/docview/1700103052/?pq-origsite=primo
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recordid: proquest1700103052
title: Regioselective aerobic oxidative Heck reactions with electronically unbiased alkenes: efficient access to α-alkyl vinylarenes.
format: Article
creator:
  • Zheng, Changwu
  • Stahl, Shannon S
subjects:
  • Alkenes–Chemistry
  • Catalysis–Chemistry
  • Electrons–Chemistry
  • Hydrocarbons, Aromatic–Chemistry
  • Oxidation-Reduction–Chemistry
  • Oxygen–Chemistry
  • Palladium–Chemistry
  • Stereoisomerism–Chemistry
  • Alkenes
  • Hydrocarbons, Aromatic
  • Palladium
  • Oxygen
ispartof: Chemical communications (Cambridge, England), August 18, 2015, Vol.51(64), pp.12771-12774
description: Branched-selective oxidative Heck coupling reactions have been developed between arylboronic acids and electronically unbiased terminal alkenes. The reactions exhibit high catalyst-controlled regioselectivity favoring the less common branched isomer. The reactions employ a catalyst composed of Pd(TFA) sub(2)/dmphen (TFA = trifluoroacetate, dmphen = 2,9-dimethyl-1,10-phenanthroline) and proceed efficiently at 45-60 degree C under 1 atm of O sub(2) without requiring other additives. A broad array of functional groups, including aryl halide, allyl silane and carboxylic acids are tolerated.
language: eng
source:
identifier: E-ISSN: 1364-548X ; DOI: 1364-548X ; DOI: 10.1039/c5cc05312a
fulltext: fulltext
issn:
  • 1364548X
  • 1364-548X
url: Link


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titleRegioselective aerobic oxidative Heck reactions with electronically unbiased alkenes: efficient access to α-alkyl vinylarenes.
creatorZheng, Changwu ; Stahl, Shannon S
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subjectAlkenes–Chemistry ; Catalysis–Chemistry ; Electrons–Chemistry ; Hydrocarbons, Aromatic–Chemistry ; Oxidation-Reduction–Chemistry ; Oxygen–Chemistry ; Palladium–Chemistry ; Stereoisomerism–Chemistry ; Alkenes ; Hydrocarbons, Aromatic ; Palladium ; Oxygen
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descriptionBranched-selective oxidative Heck coupling reactions have been developed between arylboronic acids and electronically unbiased terminal alkenes. The reactions exhibit high catalyst-controlled regioselectivity favoring the less common branched isomer. The reactions employ a catalyst composed of Pd(TFA) sub(2)/dmphen (TFA = trifluoroacetate, dmphen = 2,9-dimethyl-1,10-phenanthroline) and proceed efficiently at 45-60 degree C under 1 atm of O sub(2) without requiring other additives. A broad array of functional groups, including aryl halide, allyl silane and carboxylic acids are tolerated.
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