Issue 33, 2012
From the journal:

Organic & Biomolecular Chemistry

1,2-Nucleophilic addition of 2-(picolyl)organoboranes to nitrile, aldehyde, ketone, and amide†

Jung-Ho Sona  and  James D. Hoefelmeyer*a  

* Corresponding authors

a Department of Chemistry, University of South Dakota, 414 E. Clark St., Vermillion, SD 57069, USA
E-mail: James.Hoefelmeyer@usd.edu

Abstract

A series of 2-(picolyl)borane molecules were synthesized as products of the reaction between 2-(picolyl)lithium and R2BOMe (R = ethyl, 9-BBN, phenyl, 9-borafluorenyl). The 2-(picolyl)boranes were dimeric; whereas, monomers coordinated to LiOMe could be isolated when the synthesis was carried out in the presence of TMEDA and THF. The 2-(picolyl)boranes undergo reaction with nitriles, ketones, aldehydes, and amides with apparent 1,2-addition of the B–C(picolyl) bond to the unsaturated bond. Theoretical models reveal the presence of a donor orbital on the 2-(picolyl)borane with significant electron density at the benzylic carbon that we conclude was involved in nucleophilic attack on the electrophilic center of unsaturated organic functional groups.

Graphical abstract: 1,2-Nucleophilic addition of 2-(picolyl)organoboranes to nitrile, aldehyde, ketone, and amide

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C2OB25518A
Article type
Paper
Submitted
09 Mar 2012
Accepted
21 Jun 2012
First published
21 Jun 2012

Org. Biomol. Chem., 2012,10, 6656-6664

Permissions

Request permissions

1,2-Nucleophilic addition of 2-(picolyl)organoboranes to nitrile, aldehyde, ketone, and amide

J. Son and J. D. Hoefelmeyer, Org. Biomol. Chem., 2012, 10, 6656 DOI: 10.1039/C2OB25518A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements