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Efficient hydroxymethylation reactions of iodoarenes using CO and 1,3-dimethylimidazol-2-ylidene borane

Kawamoto, T and Okada, T and Curran, DP and Ryu, I (2013) Efficient hydroxymethylation reactions of iodoarenes using CO and 1,3-dimethylimidazol-2-ylidene borane. Organic Letters, 15 (9). 2144 - 2147. ISSN 1523-7060

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Abstract

A hydroxymethylation reaction of a variety of iodoarenes proceeded effectively in the presence of CO, NHC-borane, diMeImd-BH3 (2) as a radical mediator, and a catalytic amount of AIBN. The reaction took place chemoselectively at the aryl-iodine bond but not at the aryl-bromine and aryl-chlorine bonds. A three-component coupling reaction comprising aryl iodides, CO, and electron-deficient alkenes also proceeded well to give unsymmetrical ketones in good yields. Control experiments show that 2 would act as a hydrogen donor to acyl radicals and iodinated NHC-borane as a reducing agent of aldehydes. © 2013 American Chemical Society.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Kawamoto, T
Okada, T
Curran, DPcurran@pitt.eduCURRAN
Ryu, I
Date: 3 May 2013
Date Type: Publication
Journal or Publication Title: Organic Letters
Volume: 15
Number: 9
Page Range: 2144 - 2147
DOI or Unique Handle: 10.1021/ol4006294
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 1523-7060
PubMed ID: 23590524
Date Deposited: 05 Mar 2014 21:27
Last Modified: 02 Feb 2019 15:58
URI: http://d-scholarship.pitt.edu/id/eprint/20676

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