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Kawamoto T, Okada T, Curran DP, et al. Efficient hydroxymethylation reactions of iodoarenes using CO and 1,3-dimethylimidazol-2-ylidene borane. Org Lett. 2013;15(9):2144-7doi: 10.1021/ol4006294.
Kawamoto, T., Okada, T., Curran, D. P., & Ryu, I. (2013). Efficient hydroxymethylation reactions of iodoarenes using CO and 1,3-dimethylimidazol-2-ylidene borane. Organic letters, 15(9), 2144-7. https://doi.org/10.1021/ol4006294
Kawamoto, Takuji, et al. "Efficient hydroxymethylation reactions of iodoarenes using CO and 1,3-dimethylimidazol-2-ylidene borane." Organic letters vol. 15,9 (2013): 2144-7. doi: https://doi.org/10.1021/ol4006294
Kawamoto T, Okada T, Curran DP, Ryu I. Efficient hydroxymethylation reactions of iodoarenes using CO and 1,3-dimethylimidazol-2-ylidene borane. Org Lett. 2013 May 03;15(9):2144-7. doi: 10.1021/ol4006294. Epub 2013 Apr 16. PMID: 23590524.
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Org Lett. 2013 May 03;15(9):2144-7. doi: 10.1021/ol4006294. Epub 2013 Apr 16.

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

Organic letters

Takuji Kawamoto, Takuma Okada, Dennis P Curran, Ilhyong Ryu

Affiliations

  1. Department of Chemistry, Graduate School of Science, Osaka Prefecture University, Sakai, Osaka 599-8531, Japan.

PMID: 23590524 DOI: 10.1021/ol4006294

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.

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