Draft:Chloroform-COware Chemistry
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Chloroform-COware Chemistry is a method for conducting carbonylation reactions wherein carbon monoxide is generated ex situ from chloroform in one chamber of a two-chamber reactor (COware), and the generated CO then diffuses into the second chamber where it participates in the desired chemical transformation.[1]
The fundamental chemical principle underlying this methodology involves the generation of carbon monoxide through the hydrolysis of chloroform under basic conditions.[2] Typically, this is achieved by reacting chloroform with a strong aqueous alkali metal hydroxide, such as potassium hydroxide (KOH) or cesium hydroxide (CsOH), in one chamber of the COware reactor. This reaction proceeds via the formation of dichlorocarbene as an intermediate, which subsequently undergoes hydrolysis to yield carbon monoxide, water, and the corresponding metal chloride salt.
The "COware" Reactor Setup
[edit]The "COware" reactor setup is a key enabling technology for "Chloroform-COware Chemistry." Its design typically involves two separate glass chambers that are connected, allowing for the diffusion of gases between them.[3] One chamber serves as the carbon monoxide generator, where chloroform is hydrolyzed under basic conditions. This chamber is usually equipped with an inlet for the addition of reagents, such as the chloroform and the aqueous base. The second chamber is where the carbonylation reaction takes place, containing the substrate, catalyst, solvent, and any other necessary reagents. The connection between the two chambers allows the generated carbon monoxide gas to diffuse from the first chamber to the second, where it can participate in the chemical reaction.
Applications
[edit]Aminocarbonylation of isoquinolines: The technique has been used in the aminocarbonylation of isoquinolines and quinolines to synthesize valuable pharmaceutically relevant compounds.[1]
Carbonylative Suzuki coupling: A reaction that combines carbon monoxide insertion with a Suzuki cross-coupling reaction to form ketones.[4]
Carbonylation of phenols: Carbonylation of a wide range of medicinally relevant phenols, including both natural and synthetic derivatives, into their corresponding aryl ester.[5]
Synthesis of N-capped peptides: The method allows for the synthesis of a variety of N-capped peptides, including those with biological relevance, such as anticancer drug analogues.[6]
Key Advantages
[edit]Safety: The two-chamber system produces CO ex situ from chloroform in a closed setup, minimizing exposure risks compared to handling pure CO gas, which can be toxic.[3]
Cost-Effective & Convenient: Chloroform is a relatively inexpensive and readily available chemical, and is easier to handle than high-pressure CO or toxic surrogates (e.g., phosgene derivatives).[1]
Isotopic Labeling Compatibility: Commercially available isotopically labeled chloroform (¹³CHCl₃ and ¹⁴CHCl₃) can be readily used to synthesize isotopically labeled carbonyl compounds, valuable tools for mechanistic studies and in pharmaceutical research.[1]
References
[edit]- ^ a b c d Halder, Pallabi; Talukdar, Vishal; Iqubal, Ashif; Das, Parthasarathi (2022-11-04). "Palladium-Catalyzed Aminocarbonylation of Isoquinolines Utilizing Chloroform-COware Chemistry". The Journal of Organic Chemistry. 87 (21): 13965–13979. doi:10.1021/acs.joc.2c01629. ISSN 0022-3263.
- ^ Mondal, Krishanu; Halder, Pallabi; Gopalan, Greeshma; Sasikumar, P.; Radhakrishnan, K. V.; Das, Parthasarathi (2019-05-29). "Chloroform as a CO surrogate: applications and recent developments". Organic & Biomolecular Chemistry. 17 (21): 5212–5222. doi:10.1039/C9OB00886A. ISSN 1477-0539.
- ^ a b Friis, Stig D.; Lindhardt, Anders T.; Skrydstrup, Troels (2016-04-19). "The Development and Application of Two-Chamber Reactors and Carbon Monoxide Precursors for Safe Carbonylation Reactions". Accounts of Chemical Research. 49 (4): 594–605. doi:10.1021/acs.accounts.5b00471. ISSN 0001-4842.
- ^ Halder, Pallabi; Iqubal, Ashif; Mondal, Krishanu; Mukhopadhyay, Narottam; Das, Parthasarathi (2023-11-03). "Carbonylative Transformations Using a DMAP-Based Pd-Catalyst through Ex Situ CO Generation". The Journal of Organic Chemistry. 88 (21): 15218–15236. doi:10.1021/acs.joc.3c01725. ISSN 0022-3263.
- ^ Halder, Pallabi; Mondal, Krishanu; Jash, Arijit; Das, Parthasarathi (2024-07-05). "Exploiting Chloroform-COware Chemistry for Pd-Catalyzed Carbonylation of Naturally Occurring and Medicinally Relevant Phenols". The Journal of Organic Chemistry. 89 (13): 9275–9286. doi:10.1021/acs.joc.4c00234. ISSN 0022-3263.
- ^ Barahdia, Aman Singh; Thakare, Karuna; Jain, Rahul (2025-02-07). "Ex Situ Synthesis of N-Capped Peptides in the Solution Phase via Palladium-Catalyzed Aminocarbonylation Utilizing Chloroform-COware". The Journal of Organic Chemistry. 90 (5): 1813–1824. doi:10.1021/acs.joc.4c02404. ISSN 0022-3263.