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Xie J, Li J, Weingand V, et al. Intermolecular Photocatalyzed Heck-like Coupling of Unactivated Alkyl Bromides by a Dinuclear Gold Complex. Chemistry. 2016;22(36):12646-50doi: 10.1002/chem.201602939.
Xie, J., Li, J., Weingand, V., Rudolph, M., & Hashmi, A. S. (2016). Intermolecular Photocatalyzed Heck-like Coupling of Unactivated Alkyl Bromides by a Dinuclear Gold Complex. Chemistry (Weinheim an der Bergstrasse, Germany), 22(36), 12646-50. https://doi.org/10.1002/chem.201602939
Xie, Jin, et al. "Intermolecular Photocatalyzed Heck-like Coupling of Unactivated Alkyl Bromides by a Dinuclear Gold Complex." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 22,36 (2016): 12646-50. doi: https://doi.org/10.1002/chem.201602939
Xie J, Li J, Weingand V, Rudolph M, Hashmi AS. Intermolecular Photocatalyzed Heck-like Coupling of Unactivated Alkyl Bromides by a Dinuclear Gold Complex. Chemistry. 2016 Aug 26;22(36):12646-50. doi: 10.1002/chem.201602939. Epub 2016 Aug 01. PMID: 27348503.
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Chemistry. 2016 Aug 26;22(36):12646-50. doi: 10.1002/chem.201602939. Epub 2016 Aug 01.

Intermolecular Photocatalyzed Heck-like Coupling of Unactivated Alkyl Bromides by a Dinuclear Gold Complex.

Chemistry (Weinheim an der Bergstrasse, Germany)

Jin Xie, Jian Li, Vanessa Weingand, Matthias Rudolph, A Stephen K Hashmi

Affiliations

  1. Organisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany. [email protected].
  2. Organisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
  3. Organisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany. [email protected].
  4. Chemistry Department, Faculty of Science, King Abdulaziz University (KAU), Jeddah, 21589, Saudi Arabia. [email protected].

PMID: 27348503 DOI: 10.1002/chem.201602939

Abstract

A practical protocol for a photocatalyzed alkyl-Heck-like reaction of unactivated alkyl bromides and different alkenes promoted by dinuclear gold photoredox catalysis in the presence of an inorganic base is reported. Primary, secondary, and tertiary unactivated alkyl bromides with β-hydrogen can be applied. Esters, aldehydes, ketones, nitriles, alcohols, heterocycles, alkynes, alkenes, ethers, and halogen moieties are all well tolerated. In addition to 1,1-diarylalkenes, silylenolethers and enamides can also be applied, which further increases the synthetic potential of the reaction. The mild reaction conditions, broad substrate scope, and an excellent functional-group tolerance deliver an ideal tool for synthetic chemists that can even be used for challenging late-stage modifications of complex natural products.

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: alkenes; alkyl halides; gold; photoredox catalysis; radicals

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