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

Plain Text (licence) Available under License : See the attached license file. Download (1kB)

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.

---

Share

Citation/Export:	Select format... Citation - Text Citation - HTML Endnote BibTex Dublin Core OpenURL MARC (ISO 2709) METS MODS EP3 XML Reference Manager Refer
Social Networking:	Share |

---

Details

Item Type:	Article
Status:	Published
Creators/Authors:	Creators Email Pitt Username ORCID Kawamoto, T Okada, T Curran, DP curran@pitt.edu CURRAN 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:	12 Jun 2021 22:56
URI:	http://d-scholarship-dev.library.pitt.edu/id/eprint/20676

---

Metrics

Monthly Views for the past 3 years

Plum Analytics

Altmetric.com

---

Actions (login required)

View Item