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Generation and Synthetic Application of Trifluoromethyl Diazomethane Utilizing Continuous Flow Technologies.

Organic letters

Pieber B, Kappe CO.
PMID: 26902154
Org Lett. 2016 Mar 04;18(5):1076-9. doi: 10.1021/acs.orglett.6b00194. Epub 2016 Feb 23.

A continuous process for the synthesis and inline separation of anhydrous trifluoromethyl diazomethane in a single continuous flow process is presented. The diazo building block is generated from the corresponding amine and NaNO2 under acidic, aqueous conditions and subsequently...

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Pieber B, Kappe CO. Generation and Synthetic Application of Trifluoromethyl Diazomethane Utilizing Continuous Flow Technologies. Org Lett. 2016;18(5):1076-9doi: 10.1021/acs.orglett.6b00194.
Pieber, B., & Kappe, C. O. (2016). Generation and Synthetic Application of Trifluoromethyl Diazomethane Utilizing Continuous Flow Technologies. Organic letters, 18(5), 1076-9. https://doi.org/10.1021/acs.orglett.6b00194
Pieber, Bartholomäus, and Kappe, C Oliver. "Generation and Synthetic Application of Trifluoromethyl Diazomethane Utilizing Continuous Flow Technologies." Organic letters vol. 18,5 (2016): 1076-9. doi: https://doi.org/10.1021/acs.orglett.6b00194
Pieber B, Kappe CO. Generation and Synthetic Application of Trifluoromethyl Diazomethane Utilizing Continuous Flow Technologies. Org Lett. 2016 Mar 04;18(5):1076-9. doi: 10.1021/acs.orglett.6b00194. Epub 2016 Feb 23. PMID: 26902154.
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The First Crystal Structure of a Reactive Dirhodium Carbene Complex and a Versatile Method for the Preparation of Gold Carbenes by Rhodium-to-Gold Transmetalation.

Angewandte Chemie (International ed. in English)

Werlé C, Goddard R, Fürstner A.
PMID: 26534892
Angew Chem Int Ed Engl. 2015 Dec 14;54(51):15452-6. doi: 10.1002/anie.201506902. Epub 2015 Nov 04.

The dirhodium carbene derived from bis(4-methoxyphenyl)diazomethane and [Rh(tpa)4 ]⋅CH2 Cl2 (tpa=triphenylacetate) was characterized by UV, IR, and NMR spectroscopy, HRMS, as well as by X-ray diffraction. The isolated complex exhibits prototypical rhodium carbene reactivity in that it cyclopropanates 4-methoxystyrene...

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Werlé C, Goddard R, Fürstner A. The First Crystal Structure of a Reactive Dirhodium Carbene Complex and a Versatile Method for the Preparation of Gold Carbenes by Rhodium-to-Gold Transmetalation. Angew Chem Int Ed Engl. 2015;54(51):15452-6doi: 10.1002/anie.201506902.
Werlé, C., Goddard, R., & Fürstner, A. (2015). The First Crystal Structure of a Reactive Dirhodium Carbene Complex and a Versatile Method for the Preparation of Gold Carbenes by Rhodium-to-Gold Transmetalation. Angewandte Chemie (International ed. in English), 54(51), 15452-6. https://doi.org/10.1002/anie.201506902
Werlé, Christophe, et al. "The First Crystal Structure of a Reactive Dirhodium Carbene Complex and a Versatile Method for the Preparation of Gold Carbenes by Rhodium-to-Gold Transmetalation." Angewandte Chemie (International ed. in English) vol. 54,51 (2015): 15452-6. doi: https://doi.org/10.1002/anie.201506902
Werlé C, Goddard R, Fürstner A. The First Crystal Structure of a Reactive Dirhodium Carbene Complex and a Versatile Method for the Preparation of Gold Carbenes by Rhodium-to-Gold Transmetalation. Angew Chem Int Ed Engl. 2015 Dec 14;54(51):15452-6. doi: 10.1002/anie.201506902. Epub 2015 Nov 04. PMID: 26534892; PMCID: PMC4832834.
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Characterization of chemicals mediating ovipositional host-plant finding byAmyelois transitella females.

Journal of chemical ecology

Phelan PL, Roelofs CJ, Youngman RR, Baker TC.
PMID: 24258809
J Chem Ecol. 1991 Mar;17(3):599-613. doi: 10.1007/BF00982129.

Ovipositional host-finding in the navel orangeworm,Amyelois transitella (Walker), is brought about by an in-flight response to host odors. Wind-tunnel studies of the response of gravid females to almonds showed that this response is mediated primarily by long-chain fatty acids,...

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Phelan PL, Roelofs CJ, Youngman RR, et al. Characterization of chemicals mediating ovipositional host-plant finding byAmyelois transitella females. J Chem Ecol. 1991;17(3):599-613doi: 10.1007/BF00982129.
Phelan, P. L., Roelofs, C. J., Youngman, R. R., & Baker, T. C. (1991). Characterization of chemicals mediating ovipositional host-plant finding byAmyelois transitella females. Journal of chemical ecology, 17(3), 599-613. https://doi.org/10.1007/BF00982129
Phelan, P L, et al. "Characterization of chemicals mediating ovipositional host-plant finding byAmyelois transitella females." Journal of chemical ecology vol. 17,3 (1991): 599-613. doi: https://doi.org/10.1007/BF00982129
Phelan PL, Roelofs CJ, Youngman RR, Baker TC. Characterization of chemicals mediating ovipositional host-plant finding byAmyelois transitella females. J Chem Ecol. 1991 Mar;17(3):599-613. doi: 10.1007/BF00982129. PMID: 24258809.
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Fluoroalkyl-Substituted Diazomethanes and Their Application in a General Synthesis of Pyrazoles and Pyrazolines.

Chemistry (Weinheim an der Bergstrasse, Germany)

Mertens L, Hock KJ, Koenigs RM.
PMID: 27168358
Chemistry. 2016 Jul 04;22(28):9542-5. doi: 10.1002/chem.201601707. Epub 2016 Jun 06.

A novel continuous-flow approach for the synthesis of fluoroalkyl-substituted diazomethanes has been developed. Utilizing a cheap, self-made microreactor fluoroalkyl-substituted amines were transformed into the corresponding diazomethanes using tert-butyl nitrite and acetic acid as catalyst. These diazomethanes were employed in...

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Mertens L, Hock KJ, Koenigs RM. Fluoroalkyl-Substituted Diazomethanes and Their Application in a General Synthesis of Pyrazoles and Pyrazolines. Chemistry. 2016;22(28):9542-5doi: 10.1002/chem.201601707.
Mertens, L., Hock, K. J., & Koenigs, R. M. (2016). Fluoroalkyl-Substituted Diazomethanes and Their Application in a General Synthesis of Pyrazoles and Pyrazolines. Chemistry (Weinheim an der Bergstrasse, Germany), 22(28), 9542-5. https://doi.org/10.1002/chem.201601707
Mertens, Lucas, et al. "Fluoroalkyl-Substituted Diazomethanes and Their Application in a General Synthesis of Pyrazoles and Pyrazolines." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 22,28 (2016): 9542-5. doi: https://doi.org/10.1002/chem.201601707
Mertens L, Hock KJ, Koenigs RM. Fluoroalkyl-Substituted Diazomethanes and Their Application in a General Synthesis of Pyrazoles and Pyrazolines. Chemistry. 2016 Jul 04;22(28):9542-5. doi: 10.1002/chem.201601707. Epub 2016 Jun 06. PMID: 27168358.
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Automated library synthesis of cyclopropyl boronic esters employing diazomethane in a tube-in-tube flow reactor.

Organic & biomolecular chemistry

Koolman HF, Kantor S, Bogdan AR, Wang Y, Pan JY, Djuric SW.
PMID: 27314279
Org Biomol Chem. 2016 Jul 06;14(27):6591-5. doi: 10.1039/c6ob00715e.

The efficient synthesis of cyclopropyl boronic esters in library format using a diazomethane flow reactor has been achieved. A pivotal component of the system is a fully automated tube-in-tube reactor allowing for safe handling of hazardous diazomethane on repeated...

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Koolman HF, Kantor S, Bogdan AR, et al. Automated library synthesis of cyclopropyl boronic esters employing diazomethane in a tube-in-tube flow reactor. Org Biomol Chem. 2016;14(27):6591-5doi: 10.1039/c6ob00715e.
Koolman, H. F., Kantor, S., Bogdan, A. R., Wang, Y., Pan, J. Y., & Djuric, S. W. (2016). Automated library synthesis of cyclopropyl boronic esters employing diazomethane in a tube-in-tube flow reactor. Organic & biomolecular chemistry, 14(27), 6591-5. https://doi.org/10.1039/c6ob00715e
Koolman, Hannes F, et al. "Automated library synthesis of cyclopropyl boronic esters employing diazomethane in a tube-in-tube flow reactor." Organic & biomolecular chemistry vol. 14,27 (2016): 6591-5. doi: https://doi.org/10.1039/c6ob00715e
Koolman HF, Kantor S, Bogdan AR, Wang Y, Pan JY, Djuric SW. Automated library synthesis of cyclopropyl boronic esters employing diazomethane in a tube-in-tube flow reactor. Org Biomol Chem. 2016 Jul 06;14(27):6591-5. doi: 10.1039/c6ob00715e. PMID: 27314279.
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Determination des metabolites monoester de butylbenzyl-phthalate (bbp) par gcms dans les urines de personnes exposees: analysis of the monoester metabolites of butylbenzyl phthalate by gc-ms in urine of exposed workers.

Acta clinica Belgica

Martens F, Martens M.
PMID: 24862519
Acta Clin Belg. 2002;57:16-23. doi: 10.1179/acb.2002.071.

A method of analysis was developed to determine free and glucuronated monobutyl phthalate (BuP) and monobenzyl phthalate (BeP) in urine for the assessment of exposure of man to butylbenzyl phthalate (BBP) in the workplace and in the environment. This...

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Martens F, Martens M. Determination des metabolites monoester de butylbenzyl-phthalate (bbp) par gcms dans les urines de personnes exposees: analysis of the monoester metabolites of butylbenzyl phthalate by gc-ms in urine of exposed workers. Acta Clin Belg. 2002;57:16-23doi: 10.1179/acb.2002.071.
Martens, F., & Martens, M. (2002). Determination des metabolites monoester de butylbenzyl-phthalate (bbp) par gcms dans les urines de personnes exposees: analysis of the monoester metabolites of butylbenzyl phthalate by gc-ms in urine of exposed workers. Acta clinica Belgica, 5716-23. https://doi.org/10.1179/acb.2002.071
Martens, F, and Martens, M. "Determination des metabolites monoester de butylbenzyl-phthalate (bbp) par gcms dans les urines de personnes exposees: analysis of the monoester metabolites of butylbenzyl phthalate by gc-ms in urine of exposed workers." Acta clinica Belgica vol. 57 (2002): 16-23. doi: https://doi.org/10.1179/acb.2002.071
Martens F, Martens M. Determination des metabolites monoester de butylbenzyl-phthalate (bbp) par gcms dans les urines de personnes exposees: analysis of the monoester metabolites of butylbenzyl phthalate by gc-ms in urine of exposed workers. Acta Clin Belg. 2002;57:16-23. doi: 10.1179/acb.2002.071. PMID: 24862519.
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Synthesis of 1,2,7,7a-tetrahydro-1aH-cyclopropa[b]quinoline-1a-carboxylic acid derivatives, doubly constrained ACC derivatives, by a remarkable cyclopropanation process.

The Journal of organic chemistry

Szakonyi Z, Fülöp F, Tourwé D, De Kimpe N.
PMID: 11925228
J Org Chem. 2002 Apr 05;67(7):2192-6. doi: 10.1021/jo010993z.

Reaction of N-benzoyl-1,2,3,4-tetrahydroquinoline-2-carboxylic acid with acetic anhydride resulted in 1H,3H,5H-oxazolo[3,4-a]quinolin-3-one derivative 13. Different cyclopropanation processes were applied to 13, but only diazomethane in the presence of water furnished the hitherto unknown methyl 1,2,7,7a-tetrahydro-1aH-cyclopropa[b]quinoline-1a-carboxylate 14, which can be considered as...

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Szakonyi Z, Fülöp F, Tourwé D, et al. Synthesis of 1,2,7,7a-tetrahydro-1aH-cyclopropa[b]quinoline-1a-carboxylic acid derivatives, doubly constrained ACC derivatives, by a remarkable cyclopropanation process. J Org Chem. 2002;67(7):2192-6doi: 10.1021/jo010993z.
Szakonyi, Z., Fülöp, F., Tourwé, D., & De Kimpe, N. (2002). Synthesis of 1,2,7,7a-tetrahydro-1aH-cyclopropa[b]quinoline-1a-carboxylic acid derivatives, doubly constrained ACC derivatives, by a remarkable cyclopropanation process. The Journal of organic chemistry, 67(7), 2192-6. https://doi.org/10.1021/jo010993z
Szakonyi, Zsolt, et al. "Synthesis of 1,2,7,7a-tetrahydro-1aH-cyclopropa[b]quinoline-1a-carboxylic acid derivatives, doubly constrained ACC derivatives, by a remarkable cyclopropanation process." The Journal of organic chemistry vol. 67,7 (2002): 2192-6. doi: https://doi.org/10.1021/jo010993z
Szakonyi Z, Fülöp F, Tourwé D, De Kimpe N. Synthesis of 1,2,7,7a-tetrahydro-1aH-cyclopropa[b]quinoline-1a-carboxylic acid derivatives, doubly constrained ACC derivatives, by a remarkable cyclopropanation process. J Org Chem. 2002 Apr 05;67(7):2192-6. doi: 10.1021/jo010993z. PMID: 11925228.
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Unusual pathways for metal-assisted C[bond]C and C[bond]P coupling reactions using allenylidenerhodium complexes as precursors.

Journal of the American Chemical Society

Werner H, Wiedemann R, Laubender M, Windmüller B, Steinert P, Gevert O, Wolf J.
PMID: 12059220
J Am Chem Soc. 2002 Jun 19;124(24):6966-80. doi: 10.1021/ja012479g.

The rhodium allenylidenes trans-[RhCl[[double bond]C[double bond]C[double bond]C(Ph)R](PiPr(3))(2)] [R = Ph (1), p-Tol (2)] react with NaC(5)H(5) to give the half-sandwich type complexes [(eta(5)-C(5)H(5))Rh[[double bond]C[double bond]C[double bond]C(Ph)R](PiPr(3))] (3, 4). The reaction of 1 with the Grignard reagent CH(2)[double bond]CHMgBr affords...

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Werner H, Wiedemann R, Laubender M, et al. Unusual pathways for metal-assisted C[bond]C and C[bond]P coupling reactions using allenylidenerhodium complexes as precursors. J Am Chem Soc. 2002;124(24):6966-80doi: 10.1021/ja012479g.
Werner, H., Wiedemann, R., Laubender, M., Windmüller, B., Steinert, P., Gevert, O., & Wolf, J. (2002). Unusual pathways for metal-assisted C[bond]C and C[bond]P coupling reactions using allenylidenerhodium complexes as precursors. Journal of the American Chemical Society, 124(24), 6966-80. https://doi.org/10.1021/ja012479g
Werner, Helmut, et al. "Unusual pathways for metal-assisted C[bond]C and C[bond]P coupling reactions using allenylidenerhodium complexes as precursors." Journal of the American Chemical Society vol. 124,24 (2002): 6966-80. doi: https://doi.org/10.1021/ja012479g
Werner H, Wiedemann R, Laubender M, Windmüller B, Steinert P, Gevert O, Wolf J. Unusual pathways for metal-assisted C[bond]C and C[bond]P coupling reactions using allenylidenerhodium complexes as precursors. J Am Chem Soc. 2002 Jun 19;124(24):6966-80. doi: 10.1021/ja012479g. PMID: 12059220.
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Cycloadditions of 16-Electron 1,3-Dipoles with Ethylene. A Density Functional and CCSD(T) Study.

The Journal of organic chemistry

Su MD, Liao HY, Chung WS, Chu SY.
PMID: 11674676
J Org Chem. 1999 Sep 03;64(18):6710-6716. doi: 10.1021/jo990504j.

The 1,3-dipolar cycloaddition (DC) reactions of ethylene with nitrile ylide (CNC), nitrile imine (CNN), nitrile oxide (CNO), diazomethane (NNC), azine (NNN), and nitrous oxide (NNO) in the gas phase were examined using the density functional theory and CCSD(T) calculations....

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Su MD, Liao HY, Chung WS, et al. Cycloadditions of 16-Electron 1,3-Dipoles with Ethylene. A Density Functional and CCSD(T) Study. J Org Chem. 1999;64(18):6710-6716doi: 10.1021/jo990504j.
Su, M. D., Liao, H. Y., Chung, W. S., & Chu, S. Y. (1999). Cycloadditions of 16-Electron 1,3-Dipoles with Ethylene. A Density Functional and CCSD(T) Study. The Journal of organic chemistry, 64(18), 6710-6716. https://doi.org/10.1021/jo990504j
Su, Ming-Der, et al. "Cycloadditions of 16-Electron 1,3-Dipoles with Ethylene. A Density Functional and CCSD(T) Study." The Journal of organic chemistry vol. 64,18 (1999): 6710-6716. doi: https://doi.org/10.1021/jo990504j
Su MD, Liao HY, Chung WS, Chu SY. Cycloadditions of 16-Electron 1,3-Dipoles with Ethylene. A Density Functional and CCSD(T) Study. J Org Chem. 1999 Sep 03;64(18):6710-6716. doi: 10.1021/jo990504j. PMID: 11674676.
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A Novel Class of Conformationally Constrained, Masked Cysteines: Synthesis of 2-Alkyl- and 2-Arylsulfanyl-1-aminocyclopropanecarboxylic Acids.

The Journal of organic chemistry

Clerici F, Gelmi ML, Pocar D.
PMID: 11674139
J Org Chem. 1999 Feb 05;64(3):726-730. doi: 10.1021/jo9810011.

A convenient synthesis of 4-sulfanylmethylene-5(4H)-oxazolones 3 was realized starting from 4-(chloromethylene)oxazolone 1 and mercaptans 2. Oxazolones 3 were used as starting materials for the preparation of unknown 2-sulfanyl-1-aminocyclopropanecarboxylic acid derivatives 5 and7. Oxazolones 3 were cyclopropanated at the exocyclic...

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Clerici F, Gelmi ML, Pocar D. A Novel Class of Conformationally Constrained, Masked Cysteines: Synthesis of 2-Alkyl- and 2-Arylsulfanyl-1-aminocyclopropanecarboxylic Acids. J Org Chem. 1999;64(3):726-730doi: 10.1021/jo9810011.
Clerici, F., Gelmi, M. L., & Pocar, D. (1999). A Novel Class of Conformationally Constrained, Masked Cysteines: Synthesis of 2-Alkyl- and 2-Arylsulfanyl-1-aminocyclopropanecarboxylic Acids. The Journal of organic chemistry, 64(3), 726-730. https://doi.org/10.1021/jo9810011
Clerici, F., et al. "A Novel Class of Conformationally Constrained, Masked Cysteines: Synthesis of 2-Alkyl- and 2-Arylsulfanyl-1-aminocyclopropanecarboxylic Acids." The Journal of organic chemistry vol. 64,3 (1999): 726-730. doi: https://doi.org/10.1021/jo9810011
Clerici F, Gelmi ML, Pocar D. A Novel Class of Conformationally Constrained, Masked Cysteines: Synthesis of 2-Alkyl- and 2-Arylsulfanyl-1-aminocyclopropanecarboxylic Acids. J Org Chem. 1999 Feb 05;64(3):726-730. doi: 10.1021/jo9810011. PMID: 11674139.
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1,3-Dipolar cycloadditions of diazomethane to chiral electron-deficient olefins: the origin of the pi-facial diastereoselection.

The Journal of organic chemistry

Muray E, Alvarez-Larena A, Piniella JF, Branchadell V, Ortuno RM.
PMID: 10813946
J Org Chem. 2000 Jan 28;65(2):388-96. doi: 10.1021/jo991227j.

The stereochemical outcome of diazomethane cycloadditions to several chiral electron-deficient olefins has been investigated in order to establish the origin of the pi-facial diastereoselection. Nitro olefins, vinyl sulfones, enoates, and 2-amino enoates have been used for such a purpose....

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Muray E, Alvarez-Larena A, Piniella JF, et al. 1,3-Dipolar cycloadditions of diazomethane to chiral electron-deficient olefins: the origin of the pi-facial diastereoselection. J Org Chem. 2000;65(2):388-96doi: 10.1021/jo991227j.
Muray, E., Alvarez-Larena, A., Piniella, J. F., Branchadell, V., & Ortuno, R. M. (2000). 1,3-Dipolar cycloadditions of diazomethane to chiral electron-deficient olefins: the origin of the pi-facial diastereoselection. The Journal of organic chemistry, 65(2), 388-96. https://doi.org/10.1021/jo991227j
Muray, et al. "1,3-Dipolar cycloadditions of diazomethane to chiral electron-deficient olefins: the origin of the pi-facial diastereoselection." The Journal of organic chemistry vol. 65,2 (2000): 388-96. doi: https://doi.org/10.1021/jo991227j
Muray E, Alvarez-Larena A, Piniella JF, Branchadell V, Ortuno RM. 1,3-Dipolar cycloadditions of diazomethane to chiral electron-deficient olefins: the origin of the pi-facial diastereoselection. J Org Chem. 2000 Jan 28;65(2):388-96. doi: 10.1021/jo991227j. PMID: 10813946.
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Ab Initio Study of the Regiochemistry of 1,3-Dipolar Cycloadditions. Reactions of Diazomethane and Formonitrile Oxide with Ethene, Propene, Acrylonitrile, and Methyl Vinyl Ether.

The Journal of organic chemistry

Rastelli A, Gandolfi R, Sarzi Amadè M.
PMID: 11672394
J Org Chem. 1998 Oct 16;63(21):7425-7436. doi: 10.1021/jo9812633.

Structures and energetics of reactants and transition structures of the cycloadditions of diazomethane (DZM) and formonitrile oxide (FNO) with ethene (ET), propene (PR), acrylonitrile (ACN), and methyl vinyl ether (MVE) have been investigated with the use of ab initio...

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Rastelli A, Gandolfi R, Sarzi Amadè M. Ab Initio Study of the Regiochemistry of 1,3-Dipolar Cycloadditions. Reactions of Diazomethane and Formonitrile Oxide with Ethene, Propene, Acrylonitrile, and Methyl Vinyl Ether. J Org Chem. 1998;63(21):7425-7436doi: 10.1021/jo9812633.
Rastelli, A., Gandolfi, R., & Sarzi Amadè, M. (1998). Ab Initio Study of the Regiochemistry of 1,3-Dipolar Cycloadditions. Reactions of Diazomethane and Formonitrile Oxide with Ethene, Propene, Acrylonitrile, and Methyl Vinyl Ether. The Journal of organic chemistry, 63(21), 7425-7436. https://doi.org/10.1021/jo9812633
Rastelli, Augusto, et al. "Ab Initio Study of the Regiochemistry of 1,3-Dipolar Cycloadditions. Reactions of Diazomethane and Formonitrile Oxide with Ethene, Propene, Acrylonitrile, and Methyl Vinyl Ether." The Journal of organic chemistry vol. 63,21 (1998): 7425-7436. doi: https://doi.org/10.1021/jo9812633
Rastelli A, Gandolfi R, Sarzi Amadè M. Ab Initio Study of the Regiochemistry of 1,3-Dipolar Cycloadditions. Reactions of Diazomethane and Formonitrile Oxide with Ethene, Propene, Acrylonitrile, and Methyl Vinyl Ether. J Org Chem. 1998 Oct 16;63(21):7425-7436. doi: 10.1021/jo9812633. PMID: 11672394.
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