Abstract
| Original language | English |
|---|---|
| Pages (from-to) | 16145-16148 |
| Number of pages | 5 |
| Journal | Angewandte Chemie International Edition |
| Volume | 55 |
| Issue number | 52 |
| Early online date | 28 Nov 2016 |
| DOIs | |
| Publication status | Published - 23 Dec 2016 |
Fingerprint
Keywords
- organolithium chemistry
- imines
- organolithium reagents
- quinolines
- chemoselective addition
- deep eutectic solvents
- biorenewable
- green chemistry
- salt activation
Cite this
}
Exploiting deep eutectic solvents and organolithium reagent partnerships : chemoselective ultrafast addition to imines and quinolines under aerobic ambient temperature conditions. / Vidal, Cristian; García-Álvarez, Joaquín; Hernán-Gómez, Alberto; Kennedy, Alan R.; Hevia, Eva.
In: Angewandte Chemie International Edition, Vol. 55, No. 52, 23.12.2016, p. 16145-16148.Research output: Contribution to journal › Article
TY - JOUR
T1 - Exploiting deep eutectic solvents and organolithium reagent partnerships
T2 - chemoselective ultrafast addition to imines and quinolines under aerobic ambient temperature conditions
AU - Vidal, Cristian
AU - García-Álvarez, Joaquín
AU - Hernán-Gómez, Alberto
AU - Kennedy, Alan R.
AU - Hevia, Eva
N1 - This is the peer reviewed version of the following article: Vidal, C., García-Álvarez, J., Hernán-Gómez, A., Kennedy, A. R., & Hevia, E. (2016). Exploiting deep eutectic solvents and organolithium reagent partnerships: chemoselective ultrafast addition to imines and quinolines under aerobic ambient temperature conditions. Angewandte Chemie International Edition, which has been published in final form at https://dx.doi.org/10.1002/anie.201609929. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.
PY - 2016/12/23
Y1 - 2016/12/23
N2 - Shattering the long-held dogma that organolithium chemistry needs to be performed under inert atmospheres in toxic organic solvents, chemoselective addition of organolithium reagents to non-activated imines and quinolines has been accomplished in green, biorenewable deep eutectic solvents (DESs) at room temperature and in the presence of air, establishing a novel and sustainable access to amines. Improving on existing methods, this approach proceeds in the absence of additives; occurs without competitive enolization, reduction or coupling processes; and reactions were completed in seconds. Comparing RLi reactivities in DESs with those observed in pure glycerol or THF suggests a kinetic anionic activation of the alkylating reagents occurs, favoring nucleophilic addition over competitive hydrolysis.
AB - Shattering the long-held dogma that organolithium chemistry needs to be performed under inert atmospheres in toxic organic solvents, chemoselective addition of organolithium reagents to non-activated imines and quinolines has been accomplished in green, biorenewable deep eutectic solvents (DESs) at room temperature and in the presence of air, establishing a novel and sustainable access to amines. Improving on existing methods, this approach proceeds in the absence of additives; occurs without competitive enolization, reduction or coupling processes; and reactions were completed in seconds. Comparing RLi reactivities in DESs with those observed in pure glycerol or THF suggests a kinetic anionic activation of the alkylating reagents occurs, favoring nucleophilic addition over competitive hydrolysis.
KW - organolithium chemistry
KW - imines
KW - organolithium reagents
KW - quinolines
KW - chemoselective addition
KW - deep eutectic solvents
KW - biorenewable
KW - green chemistry
KW - salt activation
UR - http://onlinelibrary.wiley.com/journal/10.1002/(ISSN)1521-3773
U2 - 10.1002/anie.201609929
DO - 10.1002/anie.201609929
M3 - Article
VL - 55
SP - 16145
EP - 16148
JO - Angewandte Chemie International Edition
JF - Angewandte Chemie International Edition
SN - 1433-7851
IS - 52
ER -