2021
DOI: 10.3390/catal11121531
|View full text |Cite
|
Sign up to set email alerts
|

DMF as CO Surrogate in Carbonylation Reactions: Principles and Application to the Synthesis of Heterocycles

Abstract: Transition metal-catalyzed carbonylation reactions have emerged as one of the most relevant synthetic approaches for the preparation of carbonyl-containing molecules. The most commonly used protocol for the insertion of a carbonyl moiety is the use of carbon monoxide (CO) but, due to its toxic and explosive nature, this process is not suitable at an industrial scale. More recently, the chemistry of CO surrogates has received large attention as a way to use less expensive and more environmentally friendly metho… Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
4

Citation Types

0
8
0

Year Published

2022
2022
2024
2024

Publication Types

Select...
8
1

Relationship

0
9

Authors

Journals

citations
Cited by 21 publications
(8 citation statements)
references
References 67 publications
0
8
0
Order By: Relevance
“…Carbonylation is a process which refers to the introduction of either one or two molecules of carbon monoxide into the substrates to result carbonyl compounds, [2a–c] amides, [2d–e] carbamates, [2f–h] carboxylic acids, [2i–j] acyl fluorides, [2k–l] esters, [2m–n] ketoesters [2o] and their derivatives [2p–r] etc. Using various metal catalysts for this reactions Ni, [3a–d] Fe, [3e–g] Cu, [3h–i] Co, [3j–k] Rh, [3l–m] Ru [3n–o] and etc.…”
Section: Introductionmentioning
confidence: 99%
See 1 more Smart Citation
“…Carbonylation is a process which refers to the introduction of either one or two molecules of carbon monoxide into the substrates to result carbonyl compounds, [2a–c] amides, [2d–e] carbamates, [2f–h] carboxylic acids, [2i–j] acyl fluorides, [2k–l] esters, [2m–n] ketoesters [2o] and their derivatives [2p–r] etc. Using various metal catalysts for this reactions Ni, [3a–d] Fe, [3e–g] Cu, [3h–i] Co, [3j–k] Rh, [3l–m] Ru [3n–o] and etc.…”
Section: Introductionmentioning
confidence: 99%
“…Till date, several reagents, such as carbon dioxide, [10] chloroform, [11] formic acid, [12] formaldehyde and its derivatives [13] metal carbonyls, [14] methanol, [15] DMF [3c] oxalyl chloride, [16] oxalic acid derivatives, [17] silacarboxylic acids [18] and amides, [19] and others [20] have been developed as CO substitutes. various carbonyl surrogates, acetic formic anhydride (AFA) [21] and N ‐formyl saccharin (NFSac) [22] are well‐known carbon monoxide sources.…”
Section: Introductionmentioning
confidence: 99%
“…Our method provides an alternate route for the synthesis of N -aroylated amino acids that removes the need of carboxylic acid activation. Although the use of carbon monoxide gas has previously been used for palladium-catalyzed aminocarbonylation of aryl bromides employing amino acids, , the hazards associated with the use of pressurized cylinders with highly toxic and flammable carbon monoxide have prompted the development of a variety of precursors, which release carbon monoxide in situ in a controlled fashion followed by simultaneous consumption. Earlier studies describing aminocarbonylation using such carbon monoxide precursors for N-capping of amino acids have primarily employed aryl iodides, which while requiring milder conditions due to the relatively facile oxidative addition, are less common and more expensive than the aryl bromides and readily available triflates used in this work. , We decided to use molybdenum hexacarbonyl, a solid compound that is well-known to release carbon monoxide by decomposition at high temperatures or by ligand exchange in the presence of a strong base such as 1,8-diazabicyclo(5.4.0)­undec-7-ene (DBU) . As molybdenum hexacarbonyl is not inert and by itself can catalyze reactions such as the reduction of nitro groups, we utilize a two-chamber system for carbonylation .…”
Section: Introductionmentioning
confidence: 99%
“…The concept of a CO surrogate has been introduced to allow facile and safe insertion of the carbonyl group without exposure to toxic CO gas . Several CO surrogates have been put into practice in recent years, such as formic acid, carbon dioxide, DMF, metal carbonyls, silacarboxylic acids, oxalic acid, acid chlorides, formates, and others to circumvent the handling of gaseous carbon monoxide. To enrich the carbonylation chemistry, our group has primarily worked on chloroform as a CO surrogate because of its cheap availability, easy handling, and comparably less toxicity .…”
Section: Introductionmentioning
confidence: 99%