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Puttinan Meepowpan. Synthesis of tetramethylene tethered bis[N-(N'-butylimidazol-2-ylidene)] N-heterocyclic carbene using as organocatalyst in benzoin condensation. (). King Mongkut's University of Technology North Bangkok. Central Library. : , 2023.
Synthesis of tetramethylene tethered bis[N-(N'-butylimidazol-2-ylidene)] N-heterocyclic carbene using as organocatalyst in benzoin condensation
Name: Sarocha Duangdesh
Organization :
Chiang Mai University. Faculty of Science
Name: Nopawit Khamtol
Organization :
Chiang Mai University. Faculty of Science
Name: Nathaporn Cheechana
Organization :
Chiang Mai University. Faculty of Science
Name: Natthapol Akkravijitkul
Organization :
Chiang Mai University. Faculty of Science
Name: Puracheth Rithchumpont
Organization :
Chiang Mai University. Faculty of Science
Name: Puttinan Meepowpan
Organization :
Chiang Mai University. Faculty of Science
Email :
pmeepowpan@gmail.com
keyword:
N-Heterocyclic carbenes
LCSH:
Organocatalysis
LCSH:
Benzoin
LCSH:
Organic synthesis
LCSH:
Aldehydes
Abstract:
N-Heterocyclic carbenes (NHCs) have been widely employed in organic transformations including
the benzoin condensation. Benzoin condensation product, a-hydroxy ketone is synthesized from the coupling
of two aldehydes via the Breslow intermediate (umpolung of aldehyde). According to previous publications,
a number of monoNHCs were introduced as the catalyst in the benzoin condensation. On the other hand, there
were few studies on bisNHCs. Thus, we were interested in structural modification and catalytic efficiency
studies of bisNHCs for this reaction. Therefore, we successfully synthesized an imidazole-based bisNHC
precursor as tetramethylene tethered bis[N-(N-butylimidazol-2-ylidene)] hexafluorophosphate or 1,4-
bis[BIm][PF6] through facile synthetic routes to obtain the catalyst in 50% overall yield. To investigate the
catalytic efficiency, the synthesized 1,4-bis[BIm][PF6] was applied to the benzoin condensation. Aromatic
aldehydes such as benzaldehyde, p-bromobenzaldehyde, p-chlorobenzaldehyde and p-anisaldehyde were used
as the substrates along with 1,4-bis[BIm][PF6] (10-30 mol%) and Cs:CO3 as a base. In addition, we optimized
the conditions in terms of bases as well as solvents. As a result, the formation of the a-hydroxy ketones
occurred in moderate to good vields (48-81% Vields)
King Mongkut's University of Technology North Bangkok. Central Library
Address:
BANGKOK
Email:
library@kmutnb.ac.th
Created:
2023
Modified:
2023-07-04
Issued:
2023-07-04
บทความ/Article
application/pdf
BibliograpyCitation :
In Mae Fah Luang University. School of Science. The Pure and Applied Chemistry International Conference 2023 (PACCON 2023) (pp.814-819). Chiang Rai : Mae Fah Luang University
eng
©copyrights King Mongkut's University of Technology North Bangkok
RightsAccess:
ใช้เวลา
0.039523 วินาที
Sarocha Duangdesh
| Title | Contributor | Type |
|---|---|---|
| Synthesis of tetramethylene tethered bis[N-(N'-butylimidazol-2-ylidene)] N-heterocyclic carbene using as organocatalyst in benzoin condensation
มหาวิทยาลัยเทคโนโลยีพระจอมเกล้าพระนครเหนือ Sarocha Duangdesh;Nopawit Khamtol;Nathaporn Cheechana;Natthapol Akkravijitkul;Puracheth Rithchumpont;Puttinan Meepowpan | บทความ/Article |
Nopawit Khamtol
| Title | Contributor | Type |
|---|---|---|
| Synthesis of tetramethylene tethered bis[N-(N'-butylimidazol-2-ylidene)] N-heterocyclic carbene using as organocatalyst in benzoin condensation
มหาวิทยาลัยเทคโนโลยีพระจอมเกล้าพระนครเหนือ Sarocha Duangdesh;Nopawit Khamtol;Nathaporn Cheechana;Natthapol Akkravijitkul;Puracheth Rithchumpont;Puttinan Meepowpan | บทความ/Article |
Nathaporn Cheechana
| Title | Contributor | Type |
|---|---|---|
| Synthesis of tetramethylene tethered bis[N-(N'-butylimidazol-2-ylidene)] N-heterocyclic carbene using as organocatalyst in benzoin condensation
มหาวิทยาลัยเทคโนโลยีพระจอมเกล้าพระนครเหนือ Sarocha Duangdesh;Nopawit Khamtol;Nathaporn Cheechana;Natthapol Akkravijitkul;Puracheth Rithchumpont;Puttinan Meepowpan | บทความ/Article |
Natthapol Akkravijitkul
| Title | Contributor | Type |
|---|---|---|
| Synthesis of tetramethylene tethered bis[N-(N'-butylimidazol-2-ylidene)] N-heterocyclic carbene using as organocatalyst in benzoin condensation
มหาวิทยาลัยเทคโนโลยีพระจอมเกล้าพระนครเหนือ Sarocha Duangdesh;Nopawit Khamtol;Nathaporn Cheechana;Natthapol Akkravijitkul;Puracheth Rithchumpont;Puttinan Meepowpan | บทความ/Article |
Puracheth Rithchumpont
| Title | Contributor | Type |
|---|---|---|
| Synthesis of tetramethylene tethered bis[N-(N'-butylimidazol-2-ylidene)] N-heterocyclic carbene using as organocatalyst in benzoin condensation
มหาวิทยาลัยเทคโนโลยีพระจอมเกล้าพระนครเหนือ Sarocha Duangdesh;Nopawit Khamtol;Nathaporn Cheechana;Natthapol Akkravijitkul;Puracheth Rithchumpont;Puttinan Meepowpan | บทความ/Article |
Puttinan Meepowpan
| Title | Contributor | Type |
|---|---|---|
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| Synthesis and characterization of Iron(III)-Quercetin complex and its potential application for differentiation of circulating proangiogenic cells derived from peripheral blood mononuclear cells
มหาวิทยาลัยเทคโนโลยีพระจอมเกล้าพระนครเหนือ Phakorn Papan;Jiraporn Kantapan;Padchanee Sangthong;Puttinan Meepowpan;Nathupakorn Dechsupa | บทความ/Article | |
| Anti-breast cancer activity of 2',4'-Dihydroxy-6'-methoxy-3',5'-dimethylchalcone and Its derivatives from Syzygium nervosum
มหาวิทยาลัยเทคโนโลยีพระจอมเกล้าพระนครเหนือ Pornthip Chawapun;Puttinan Meepowpan;Nathupakorn Dechsupa;Jiraporn Kantapan;Padchanee Sangthong | บทความ/Article | |
| Synthesis of tetramethylene tethered bis[N-(N'-butylimidazol-2-ylidene)] N-heterocyclic carbene using as organocatalyst in benzoin condensation
มหาวิทยาลัยเทคโนโลยีพระจอมเกล้าพระนครเหนือ Sarocha Duangdesh;Nopawit Khamtol;Nathaporn Cheechana;Natthapol Akkravijitkul;Puracheth Rithchumpont;Puttinan Meepowpan | บทความ/Article | |
| Applications of methyl itaconate-anthracene adducts as chiral resolving agents for binaphthol derivatives
มหาวิทยาลัยเทคโนโลยีพระจอมเกล้าพระนครเหนือ Wichai Saema;Puracheth Rithchumpon;Nopawit Khamto;Puttinan Meepowpan | บทความ/Article |