Achieving Moderate Pressures in Sealed Vessels Using Dry Ice As a Solid CO2 Source

Overview

Journal J Vis Exp

Specialties Biology
General Medicine

Date 2018 Sep 4

PMID 30176024

Citations 5

Authors

Mohit Kapoor

Pratibha Chand-Thakuri

Justin M Maxwell

Michael C Young

Affiliations

Soon will be listed here.

Abstract

Herein is presented a general strategy to perform reactions under mild to moderate CO2 pressures with dry ice. This technique obviates the need for specialized equipment to achieve modest pressures, and can even be used to achieve higher pressures in more specialized equipment and sturdier reaction vessels. At the end of the reaction, the vials can be easily depressurized by opening at room temperature. In the present example CO2 serves as both a putative directing group as well as a way to passivate amine substrates, thereby preventing oxidation during the organometallic reaction. In addition to being easily added, the directing group is also removed under vacuum, obviating the need for extensive purification to remove the directing group. This strategy allows the facile γ-C(sp)-H arylation of aliphatic amines and has the potential to be applied to a variety of other amine-based reactions.

Citing Articles

Transforming Growth Factor β1 Ameliorates Microglial Activation in Perioperative Neurocognitive Disorders.

Lin D, Sun Y, Wang Y, Yang D, Shui M, Wang Y Neurochem Res. 2023; 48(12):3512-3524.

PMID: 37470907 DOI: 10.1007/s11064-023-03994-w.

Pon1 Deficiency Promotes Trem2 Pathway-Mediated Microglial Phagocytosis and Inhibits Pro-inflammatory Cytokines Release In Vitro and In Vivo.

Zhang L, Dong W, Ma Y, Bai L, Zhang X, Sun C Mol Neurobiol. 2022; 59(7):4612-4629.

PMID: 35589918 DOI: 10.1007/s12035-022-02827-1.

Possible role of arginase 1 positive microglia on depressive/anxiety-like behaviors in atopic dermatitis mouse model.

Yang B, Ryu J, Rim C, Shin J, Kwon M Arch Pharm Res. 2022; 45(1):11-28.

PMID: 35060088 DOI: 10.1007/s12272-022-01369-3.

Palladium-Catalyzed Regioselective Arylation of Unprotected Allylamines.

Landge V, Maxwell J, Chand-Thakuri P, Kapoor M, Diemler E, Young M JACS Au. 2021; 1(1):13-22.

PMID: 34467268 PMC: 8395680. DOI: 10.1021/jacsau.0c00003.

TRAF6 Contributes to CFA-Induced Spinal Microglial Activation and Chronic Inflammatory Pain in Mice.

Lu Y, Cao D, Ma L, Gao Y Cell Mol Neurobiol. 2021; 42(5):1543-1555.

PMID: 33694132 PMC: 11421757. DOI: 10.1007/s10571-021-01045-y.

References

North M, Pasquale R . Mechanism of cyclic carbonate synthesis from epoxides and CO2. Angew Chem Int Ed Engl. 2009; 48(16):2946-8. PMC: 2898159. DOI: 10.1002/anie.200805451. View

Gockel S, Hull K . Chloroform as a Carbon Monoxide Precursor: In or Ex Situ Generation of CO for Pd-Catalyzed Aminocarbonylations. Org Lett. 2015; 17(13):3236-9. DOI: 10.1021/acs.orglett.5b01385. View

Schettino V, Bini R . Constraining molecules at the closest approach: chemistry at high pressure. Chem Soc Rev. 2007; 36(6):869-80. DOI: 10.1039/b515964b. View

Coomber C, Benhamou L, Bucar D, Smith P, Porter M, Sheppard T . Silver-Free Palladium-Catalyzed C(sp)-H Arylation of Saturated Bicyclic Amine Scaffolds. J Org Chem. 2017; 83(5):2495-2503. DOI: 10.1021/acs.joc.7b02665. View

Mo F, Dong G . C-H bond activation. Regioselective ketone α-alkylation with simple olefins via dual activation. Science. 2014; 345(6192):68-72. DOI: 10.1126/science.1254465. View

Kapoor M, Liu D, Young M . Carbon Dioxide-Mediated C(sp)-H Arylation of Amine Substrates. J Am Chem Soc. 2018; 140(22):6818-6822. DOI: 10.1021/jacs.8b05061. View

Morimoto T, Kakiuchi K . Evolution of carbonylation catalysis: no need for carbon monoxide. Angew Chem Int Ed Engl. 2004; 43(42):5580-8. DOI: 10.1002/anie.200301736. View

Wan Y, Alterman M, Larhed M, Hallberg A . Dimethylformamide as a carbon monoxide source in fast palladium-catalyzed aminocarbonylations of aryl bromides. J Org Chem. 2002; 67(17):6232-5. DOI: 10.1021/jo025965a. View

Xu Y, Young M, Wang C, Magness D, Dong G . Catalytic C(sp(3) )-H Arylation of Free Primary Amines with an exo Directing Group Generated In Situ. Angew Chem Int Ed Engl. 2016; 55(31):9084-7. DOI: 10.1002/anie.201604268. View

10.

Julia-Hernandez F, Moragas T, Cornella J, Martin R . Remote carboxylation of halogenated aliphatic hydrocarbons with carbon dioxide. Nature. 2017; 545(7652):84-88. DOI: 10.1038/nature22316. View

11.

Chabolla S, Yang J . For CO Reduction, Hydrogen-Bond Donors Do the Trick. ACS Cent Sci. 2018; 4(3):315-317. PMC: 5879483. DOI: 10.1021/acscentsci.8b00087. View

12.

Yeung C, Dong V . Beyond Aresta's complex: Ni- and Pd-catalyzed organozinc coupling with CO2. J Am Chem Soc. 2008; 130(25):7826-7. DOI: 10.1021/ja803435w. View

13.

Kim D, Kley C, Li Y, Yang P . Copper nanoparticle ensembles for selective electroreduction of CO to C-C products. Proc Natl Acad Sci U S A. 2017; 114(40):10560-10565. PMC: 5635920. DOI: 10.1073/pnas.1711493114. View

14.

Mei T, Wang X, Yu J . Pd(II)-catalyzed amination of C-H bonds using single-electron or two-electron oxidants. J Am Chem Soc. 2009; 131(31):10806-7. DOI: 10.1021/ja904709b. View

15.

Hancu D, Green J, Beckman E . H(2)O(2) in CO(2): sustainable production and green reactions. Acc Chem Res. 2002; 35(9):757-64. DOI: 10.1021/ar010069r. View

16.

Wang D, Astruc D . The golden age of transfer hydrogenation. Chem Rev. 2015; 115(13):6621-86. DOI: 10.1021/acs.chemrev.5b00203. View

17.

Zheng Y, Song W, Zhu Y, Wei B, Xuan L . Pd-Catalyzed Acetoxylation of γ-C(sp)-H Bonds of Amines Directed by a Removable Bts-Protecting Group. J Org Chem. 2018; 83(4):2448-2454. DOI: 10.1021/acs.joc.7b02995. View

18.

Wang H, Dong B, Wang Y, Li J, Shi Y . A palladium-catalyzed regioselective hydroesterification of alkenylphenols to lactones with phenyl formate as CO source. Org Lett. 2014; 16(1):186-9. DOI: 10.1021/ol403171p. View

19.

Luo J, Larrosa I . C-H Carboxylation of Aromatic Compounds through CO Fixation. ChemSusChem. 2017; 10(17):3317-3332. PMC: 5601192. DOI: 10.1002/cssc.201701058. View

20.

Wu Y, Chen Y, Liu T, Eastgate M, Yu J . Pd-Catalyzed γ-C(sp)-H Arylation of Free Amines Using a Transient Directing Group. J Am Chem Soc. 2016; 138(44):14554-14557. PMC: 5535771. DOI: 10.1021/jacs.6b09653. View