Abstract
Tri(1-naphthyl)phosphine (Np3P) has been easily prepared in 34% yield from red phosphorus and 1-bromonaphthalene in the superbasic system t-BuONa/DMSO. The expedient procedures for the synthesis of aryl acetylenes by Sonogashira coupling of aryl iodides with terminal alkynes using Np3P as a ligand have been developed. For the first time, it is found that the reaction with compounds containing electron-donating substituents preferably affords buta-1,3-diynes.
| Original language | English |
|---|---|
| Article number | e21443 |
| Journal | Heteroatom Chemistry |
| Volume | 29 |
| Issue number | 4 |
| DOIs | |
| Publication status | Published - 1 Jul 2018 |
| Externally published | Yes |
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Keywords
- 1-bromonaphthalene
- Sonogashira coupling
- superbasic system
- tri(1-naphthyl)phosphine
ASJC Scopus subject areas
- Chemistry(all)
Cite this
Tri(1-naphthyl)phosphine as a ligand in palladium-free Sonogashira cross-coupling of arylhalogenides with acetylenes. / Govdi, Anastasiya I.; Vasilevsky, Sergey F.; Malysheva, Svetlana F.; Kazheva, Olga N.; Dyachenko, Oleg A.; Kuimov, Vladimir A.
In: Heteroatom Chemistry, Vol. 29, No. 4, e21443, 01.07.2018.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Tri(1-naphthyl)phosphine as a ligand in palladium-free Sonogashira cross-coupling of arylhalogenides with acetylenes
AU - Govdi, Anastasiya I.
AU - Vasilevsky, Sergey F.
AU - Malysheva, Svetlana F.
AU - Kazheva, Olga N.
AU - Dyachenko, Oleg A.
AU - Kuimov, Vladimir A.
PY - 2018/7/1
Y1 - 2018/7/1
N2 - Tri(1-naphthyl)phosphine (Np3P) has been easily prepared in 34% yield from red phosphorus and 1-bromonaphthalene in the superbasic system t-BuONa/DMSO. The expedient procedures for the synthesis of aryl acetylenes by Sonogashira coupling of aryl iodides with terminal alkynes using Np3P as a ligand have been developed. For the first time, it is found that the reaction with compounds containing electron-donating substituents preferably affords buta-1,3-diynes.
AB - Tri(1-naphthyl)phosphine (Np3P) has been easily prepared in 34% yield from red phosphorus and 1-bromonaphthalene in the superbasic system t-BuONa/DMSO. The expedient procedures for the synthesis of aryl acetylenes by Sonogashira coupling of aryl iodides with terminal alkynes using Np3P as a ligand have been developed. For the first time, it is found that the reaction with compounds containing electron-donating substituents preferably affords buta-1,3-diynes.
KW - 1-bromonaphthalene
KW - Sonogashira coupling
KW - superbasic system
KW - tri(1-naphthyl)phosphine
UR - http://www.scopus.com/inward/record.url?scp=85055530853&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85055530853&partnerID=8YFLogxK
U2 - 10.1002/hc.21443
DO - 10.1002/hc.21443
M3 - Article
VL - 29
JO - Heteroatom Chemistry
JF - Heteroatom Chemistry
SN - 1042-7163
IS - 4
M1 - e21443
ER -