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Convenient iron-catalyzed reductive aminations without hydrogen for selective synthesis of N-methylamines.

Nature communications

Natte K, Neumann H, Jagadeesh RV, Beller M.
PMID: 29116077
Nat Commun. 2017 Nov 07;8(1):1344. doi: 10.1038/s41467-017-01428-0.

N-Methylated amines play an important role in regulating the biological and pharmaceutical properties of all kinds of life science molecules. In general, this class of compounds is synthesized via reductive amination reactions using high pressure of molecular hydrogen. Thus,...

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Natte K, Neumann H, Jagadeesh RV, et al. Convenient iron-catalyzed reductive aminations without hydrogen for selective synthesis of N-methylamines. Nat Commun. 2017;8(1):1344doi: 10.1038/s41467-017-01428-0.
Natte, K., Neumann, H., Jagadeesh, R. V., & Beller, M. (2017). Convenient iron-catalyzed reductive aminations without hydrogen for selective synthesis of N-methylamines. Nature communications, 8(1), 1344. https://doi.org/10.1038/s41467-017-01428-0
Natte, Kishore, et al. "Convenient iron-catalyzed reductive aminations without hydrogen for selective synthesis of N-methylamines." Nature communications vol. 8,1 (2017): 1344. doi: https://doi.org/10.1038/s41467-017-01428-0
Natte K, Neumann H, Jagadeesh RV, Beller M. Convenient iron-catalyzed reductive aminations without hydrogen for selective synthesis of N-methylamines. Nat Commun. 2017 Nov 07;8(1):1344. doi: 10.1038/s41467-017-01428-0. PMID: 29116077; PMCID: PMC5677081.
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Pulses of ammonia and methylamine induce down-regulation of nematocyte and nerve cell populations in Hydrozoa (Hydra; Hydractinia).

Roux's archives of developmental biology : the official organ of the EDBO

Lange RG, Holzenburg P, Müller WA.
PMID: 28305539
Rouxs Arch Dev Biol. 1990 Nov;199(3):123-133. doi: 10.1007/BF01681485.

Hydrozoa replace used-up nematocytes (cnidocytes) by proliferation and differentiation from interstitial stem cells (i cells). Repeated pulsed exposure ofHydra to elevated levels of unprotonated ammonia leads to successive loss of the various types of nematocytes: first of the stenoteles,...

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Lange RG, Holzenburg P, Müller WA. Pulses of ammonia and methylamine induce down-regulation of nematocyte and nerve cell populations in Hydrozoa (Hydra; Hydractinia). Rouxs Arch Dev Biol. 1990;199(3):123-133doi: 10.1007/BF01681485.
Lange, R. G., Holzenburg, P., & Müller, W. A. (1990). Pulses of ammonia and methylamine induce down-regulation of nematocyte and nerve cell populations in Hydrozoa (Hydra; Hydractinia). Roux's archives of developmental biology : the official organ of the EDBO, 199(3), 123-133. https://doi.org/10.1007/BF01681485
Lange, Rolf G, et al. "Pulses of ammonia and methylamine induce down-regulation of nematocyte and nerve cell populations in Hydrozoa (Hydra; Hydractinia)." Roux's archives of developmental biology : the official organ of the EDBO vol. 199,3 (1990): 123-133. doi: https://doi.org/10.1007/BF01681485
Lange RG, Holzenburg P, Müller WA. Pulses of ammonia and methylamine induce down-regulation of nematocyte and nerve cell populations in Hydrozoa (Hydra; Hydractinia). Rouxs Arch Dev Biol. 1990 Nov;199(3):123-133. doi: 10.1007/BF01681485. PMID: 28305539.
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Direct Catalytic Asymmetric α-Allylic Alkylation of Aza-aryl Methylamines by Chiral-Aldehyde-Involved Ternary Catalysis System.

Organic letters

Zhu F, Shen QW, Wang WZ, Wu ZL, Cai T, Wen W, Guo QX.
PMID: 33544606
Org Lett. 2021 Feb 19;23(4):1463-1467. doi: 10.1021/acs.orglett.1c00143. Epub 2021 Feb 05.

A ternary catalytic system comprising a chiral aldehyde, a transition metal, and a Lewis acid is rationally designed for the asymmetric α-allylic alkylation reaction of aza-aryl methylamines and π-allylmetal electrophiles. Structural diversity chiral amines bearing carbon-carbon double bonds and...

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Zhu F, Shen QW, Wang WZ, et al. Direct Catalytic Asymmetric α-Allylic Alkylation of Aza-aryl Methylamines by Chiral-Aldehyde-Involved Ternary Catalysis System. Org Lett. 2021;23(4):1463-1467doi: 10.1021/acs.orglett.1c00143.
Zhu, F., Shen, Q. W., Wang, W. Z., Wu, Z. L., Cai, T., Wen, W., & Guo, Q. X. (2021). Direct Catalytic Asymmetric α-Allylic Alkylation of Aza-aryl Methylamines by Chiral-Aldehyde-Involved Ternary Catalysis System. Organic letters, 23(4), 1463-1467. https://doi.org/10.1021/acs.orglett.1c00143
Zhu, Fang, et al. "Direct Catalytic Asymmetric α-Allylic Alkylation of Aza-aryl Methylamines by Chiral-Aldehyde-Involved Ternary Catalysis System." Organic letters vol. 23,4 (2021): 1463-1467. doi: https://doi.org/10.1021/acs.orglett.1c00143
Zhu F, Shen QW, Wang WZ, Wu ZL, Cai T, Wen W, Guo QX. Direct Catalytic Asymmetric α-Allylic Alkylation of Aza-aryl Methylamines by Chiral-Aldehyde-Involved Ternary Catalysis System. Org Lett. 2021 Feb 19;23(4):1463-1467. doi: 10.1021/acs.orglett.1c00143. Epub 2021 Feb 05. PMID: 33544606.
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Computational studies of aliphatic amine basicity.

The Journal of organic chemistry

Caskey DC, Damrauer R, McGoff D.
PMID: 12126393
J Org Chem. 2002 Jul 26;67(15):5098-105. doi: 10.1021/jo011118g.

Computational studies have been used to examine the structural and energetic effects of adding small numbers of water molecules to ammonia, methylamine, dimethylamine, and trimethylamine, and their respective ammoniums ions using the effective fragment potential method. Distinct structural effects...

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Caskey DC, Damrauer R, McGoff D. Computational studies of aliphatic amine basicity. J Org Chem. 2002;67(15):5098-105doi: 10.1021/jo011118g.
Caskey, D. C., Damrauer, R., & McGoff, D. (2002). Computational studies of aliphatic amine basicity. The Journal of organic chemistry, 67(15), 5098-105. https://doi.org/10.1021/jo011118g
Caskey, Douglas C, et al. "Computational studies of aliphatic amine basicity." The Journal of organic chemistry vol. 67,15 (2002): 5098-105. doi: https://doi.org/10.1021/jo011118g
Caskey DC, Damrauer R, McGoff D. Computational studies of aliphatic amine basicity. J Org Chem. 2002 Jul 26;67(15):5098-105. doi: 10.1021/jo011118g. PMID: 12126393.
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Copper(II)-Catalyzed Selective Reductive Methylation of Amines with Formic Acid: An Option for Indirect Utilization of CO.

Organic letters

Qiao C, Liu XF, Liu X, He LN.
PMID: 28263072
Org Lett. 2017 Mar 17;19(6):1490-1493. doi: 10.1021/acs.orglett.7b00551. Epub 2017 Mar 06.

A copper-catalyzed protocol for reductive methylation of amines and imine with formic acid as a C1 source and phenylsilane as a reductant is reported for the first time, affording the corresponding methylamines in good to excellent yields under mild...

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Qiao C, Liu XF, Liu X, et al. Copper(II)-Catalyzed Selective Reductive Methylation of Amines with Formic Acid: An Option for Indirect Utilization of CO. Org Lett. 2017;19(6):1490-1493doi: 10.1021/acs.orglett.7b00551.
Qiao, C., Liu, X. F., Liu, X., & He, L. N. (2017). Copper(II)-Catalyzed Selective Reductive Methylation of Amines with Formic Acid: An Option for Indirect Utilization of CO. Organic letters, 19(6), 1490-1493. https://doi.org/10.1021/acs.orglett.7b00551
Qiao, Chang, et al. "Copper(II)-Catalyzed Selective Reductive Methylation of Amines with Formic Acid: An Option for Indirect Utilization of CO." Organic letters vol. 19,6 (2017): 1490-1493. doi: https://doi.org/10.1021/acs.orglett.7b00551
Qiao C, Liu XF, Liu X, He LN. Copper(II)-Catalyzed Selective Reductive Methylation of Amines with Formic Acid: An Option for Indirect Utilization of CO. Org Lett. 2017 Mar 17;19(6):1490-1493. doi: 10.1021/acs.orglett.7b00551. Epub 2017 Mar 06. PMID: 28263072.
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Amino acids as well as polyols and methylamines accumulated in rat kidney during dehydration.

Amino acids

Nakanishi T, Uyama O, Sugita M.
PMID: 24193025
Amino Acids. 1992 Jun;3(2):131-8. doi: 10.1007/BF00806778.

During antidiuresis cells in the renal inner medulla contain large amounts of sorbitol, myo-inositol, glycerophosphorylcholine and betaine to adjust the intracellular osmolality to the extracellular hyperosmolality. Although the accumulation of these four major organic osmolytes in the inner medulla...

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Nakanishi T, Uyama O, Sugita M. Amino acids as well as polyols and methylamines accumulated in rat kidney during dehydration. Amino Acids. 1992;3(2):131-8doi: 10.1007/BF00806778.
Nakanishi, T., Uyama, O., & Sugita, M. (1992). Amino acids as well as polyols and methylamines accumulated in rat kidney during dehydration. Amino acids, 3(2), 131-8. https://doi.org/10.1007/BF00806778
Nakanishi, T, et al. "Amino acids as well as polyols and methylamines accumulated in rat kidney during dehydration." Amino acids vol. 3,2 (1992): 131-8. doi: https://doi.org/10.1007/BF00806778
Nakanishi T, Uyama O, Sugita M. Amino acids as well as polyols and methylamines accumulated in rat kidney during dehydration. Amino Acids. 1992 Jun;3(2):131-8. doi: 10.1007/BF00806778. PMID: 24193025.
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Copper/diethyl azodicarboxylate mediated regioselective alkynylation of unactivated aliphatic tertiary methylamine with terminal alkyne.

Organic letters

Xu X, Li X.
PMID: 19159324
Org Lett. 2009 Feb 19;11(4):1027-9. doi: 10.1021/ol802974b.

Mediated by copper/diethyl azodicarboxylate, regioselective alkynylation of unactivated aliphatic tertiary methylamine with terminal alkyne was successfully established. It is not necessary for the tertiary methylamines to be aryl substituted to modulate the properties of amines. The alkynylation reaction described...

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Xu X, Li X. Copper/diethyl azodicarboxylate mediated regioselective alkynylation of unactivated aliphatic tertiary methylamine with terminal alkyne. Org Lett. 2009;11(4):1027-9doi: 10.1021/ol802974b.
Xu, X., & Li, X. (2009). Copper/diethyl azodicarboxylate mediated regioselective alkynylation of unactivated aliphatic tertiary methylamine with terminal alkyne. Organic letters, 11(4), 1027-9. https://doi.org/10.1021/ol802974b
Xu, Xiaoliang, and Li, Xiaonian. "Copper/diethyl azodicarboxylate mediated regioselective alkynylation of unactivated aliphatic tertiary methylamine with terminal alkyne." Organic letters vol. 11,4 (2009): 1027-9. doi: https://doi.org/10.1021/ol802974b
Xu X, Li X. Copper/diethyl azodicarboxylate mediated regioselective alkynylation of unactivated aliphatic tertiary methylamine with terminal alkyne. Org Lett. 2009 Feb 19;11(4):1027-9. doi: 10.1021/ol802974b. PMID: 19159324.
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Isolation and characterization of a moderately halophilic methanogen from a solar saltern.

Applied and environmental microbiology

Mathrani IM, Boone DR.
PMID: 16346832
Appl Environ Microbiol. 1985 Jul;50(1):140-3. doi: 10.1128/aem.50.1.140-143.1985.

A moderately halophilic methanogenic bacterium was enriched with trimethylamine and isolated from the sediment of a solar salt pond (total dissolved solids of pond water, 250 g/liter; pH 7.5). The isolate (strain SF1, DSM 3243) was an irregular coccus...

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Mathrani IM, Boone DR. Isolation and characterization of a moderately halophilic methanogen from a solar saltern. Appl Environ Microbiol. 1985;50(1):140-3doi: 10.1128/aem.50.1.140-143.1985.
Mathrani, I. M., & Boone, D. R. (1985). Isolation and characterization of a moderately halophilic methanogen from a solar saltern. Applied and environmental microbiology, 50(1), 140-3. https://doi.org/10.1128/aem.50.1.140-143.1985
Mathrani, I M, and Boone, D R. "Isolation and characterization of a moderately halophilic methanogen from a solar saltern." Applied and environmental microbiology vol. 50,1 (1985): 140-3. doi: https://doi.org/10.1128/aem.50.1.140-143.1985
Mathrani IM, Boone DR. Isolation and characterization of a moderately halophilic methanogen from a solar saltern. Appl Environ Microbiol. 1985 Jul;50(1):140-3. doi: 10.1128/aem.50.1.140-143.1985. PMID: 16346832; PMCID: PMC238586.
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Populations of methanogenic bacteria in a georgia salt marsh.

Applied and environmental microbiology

Franklin MJ, Wiebe WJ, Whitman WB.
PMID: 16347628
Appl Environ Microbiol. 1988 May;54(5):1151-7. doi: 10.1128/aem.54.5.1151-1157.1988.

Methanogens represented about 0.5% of the total bacteria in sediments from a Georgia salt marsh in which Spartina alterniflora is the predominant vegetation. The population of methanogens was composed of at least two groups of nearly equal size. One...

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Franklin MJ, Wiebe WJ, Whitman WB. Populations of methanogenic bacteria in a georgia salt marsh. Appl Environ Microbiol. 1988;54(5):1151-7doi: 10.1128/aem.54.5.1151-1157.1988.
Franklin, M. J., Wiebe, W. J., & Whitman, W. B. (1988). Populations of methanogenic bacteria in a georgia salt marsh. Applied and environmental microbiology, 54(5), 1151-7. https://doi.org/10.1128/aem.54.5.1151-1157.1988
Franklin, M J, et al. "Populations of methanogenic bacteria in a georgia salt marsh." Applied and environmental microbiology vol. 54,5 (1988): 1151-7. doi: https://doi.org/10.1128/aem.54.5.1151-1157.1988
Franklin MJ, Wiebe WJ, Whitman WB. Populations of methanogenic bacteria in a georgia salt marsh. Appl Environ Microbiol. 1988 May;54(5):1151-7. doi: 10.1128/aem.54.5.1151-1157.1988. PMID: 16347628; PMCID: PMC202619.
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In situ quantitative determination of the intermolecular attraction between amines and a graphene surface using atomic force microscopy.

Journal of colloid and interface science

Zhang Y, Zhu X, Li X, Chen B.
PMID: 32771747
J Colloid Interface Sci. 2021 Jan 01;581:385-395. doi: 10.1016/j.jcis.2020.07.112. Epub 2020 Jul 26.

The adsorption of pollutants on carbonaceous environmental media has been widely studied via batch sorption experiments and spectroscopic characterization. However, the molecular interactions between pollutants and interfacial sites on carbonaceous materials have only been indirectly investigated. To comprehend the...

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Zhang Y, Zhu X, Li X, et al. In situ quantitative determination of the intermolecular attraction between amines and a graphene surface using atomic force microscopy. J Colloid Interface Sci. 2020;581:385-395doi: 10.1016/j.jcis.2020.07.112.
Zhang, Y., Zhu, X., Li, X., & Chen, B. (2021). In situ quantitative determination of the intermolecular attraction between amines and a graphene surface using atomic force microscopy. Journal of colloid and interface science, 581385-395. https://doi.org/10.1016/j.jcis.2020.07.112
Zhang, Yuyao, et al. "In situ quantitative determination of the intermolecular attraction between amines and a graphene surface using atomic force microscopy." Journal of colloid and interface science vol. 581 (2021): 385-395. doi: https://doi.org/10.1016/j.jcis.2020.07.112
Zhang Y, Zhu X, Li X, Chen B. In situ quantitative determination of the intermolecular attraction between amines and a graphene surface using atomic force microscopy. J Colloid Interface Sci. 2021 Jan 01;581:385-395. doi: 10.1016/j.jcis.2020.07.112. Epub 2020 Jul 26. PMID: 32771747.
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The complete genome sequence of the methanogenic archaeon ISO4-H5 provides insights into the methylotrophic lifestyle of a ruminal representative of the Methanomassiliicoccales.

Standards in genomic sciences

Li Y, Leahy SC, Jeyanathan J, Henderson G, Cox F, Altermann E, Kelly WJ, Lambie SC, Janssen PH, Rakonjac J, Attwood GT.
PMID: 27602181
Stand Genomic Sci. 2016 Sep 06;11(1):59. doi: 10.1186/s40793-016-0183-5. eCollection 2016.

Methane emissions from agriculture represent around 9 % of global anthropogenic greenhouse emissions. The single largest source of this methane is animal enteric fermentation, predominantly from ruminant livestock where it is produced mainly in their fermentative forestomach (or reticulo-rumen)...

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Li Y, Leahy SC, Jeyanathan J, et al. The complete genome sequence of the methanogenic archaeon ISO4-H5 provides insights into the methylotrophic lifestyle of a ruminal representative of the Methanomassiliicoccales. Stand Genomic Sci. 2016;11(1):59doi: 10.1186/s40793-016-0183-5.
Li, Y., Leahy, S. C., Jeyanathan, J., Henderson, G., Cox, F., Altermann, E., Kelly, W. J., Lambie, S. C., Janssen, P. H., Rakonjac, J., & Attwood, G. T. (2016). The complete genome sequence of the methanogenic archaeon ISO4-H5 provides insights into the methylotrophic lifestyle of a ruminal representative of the Methanomassiliicoccales. Standards in genomic sciences, 11(1), 59. https://doi.org/10.1186/s40793-016-0183-5
Li, Yang, et al. "The complete genome sequence of the methanogenic archaeon ISO4-H5 provides insights into the methylotrophic lifestyle of a ruminal representative of the Methanomassiliicoccales." Standards in genomic sciences vol. 11,1 (2016): 59. doi: https://doi.org/10.1186/s40793-016-0183-5
Li Y, Leahy SC, Jeyanathan J, Henderson G, Cox F, Altermann E, Kelly WJ, Lambie SC, Janssen PH, Rakonjac J, Attwood GT. The complete genome sequence of the methanogenic archaeon ISO4-H5 provides insights into the methylotrophic lifestyle of a ruminal representative of the Methanomassiliicoccales. Stand Genomic Sci. 2016 Sep 06;11(1):59. doi: 10.1186/s40793-016-0183-5. eCollection 2016. PMID: 27602181; PMCID: PMC5011839.
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Regulatory factors associated with synthesis of the osmolyte glycine betaine in the halophilic methanoarchaeon Methanohalophilus portucalensis.

Applied and environmental microbiology

Chuang MJ, Lai MC, Yang DR.
PMID: 9925623
Appl Environ Microbiol. 1999 Feb;65(2):828-33. doi: 10.1128/AEM.65.2.828-833.1999.
Free PMC Article

The halophilic methanoarchaeon Methanohalophilus portucalensis can synthesize de novo and accumulate beta-glutamine, Nepsilon-acetyl-beta-lysine, and glycine betaine (betaine) as compatible solutes (osmolytes) when grown at elevated salt concentrations. Both in vivo and in vitro betaine formation assays in this study...

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Chuang MJ, Lai MC, Yang DR. Regulatory factors associated with synthesis of the osmolyte glycine betaine in the halophilic methanoarchaeon Methanohalophilus portucalensis. Appl Environ Microbiol. 1999;65(2):828-33doi: 10.1128/AEM.65.2.828-833.1999.
Chuang, M. J., Lai, M. C., & Yang, D. R. (1999). Regulatory factors associated with synthesis of the osmolyte glycine betaine in the halophilic methanoarchaeon Methanohalophilus portucalensis. Applied and environmental microbiology, 65(2), 828-33. https://doi.org/10.1128/AEM.65.2.828-833.1999
Chuang, M J, et al. "Regulatory factors associated with synthesis of the osmolyte glycine betaine in the halophilic methanoarchaeon Methanohalophilus portucalensis." Applied and environmental microbiology vol. 65,2 (1999): 828-33. doi: https://doi.org/10.1128/AEM.65.2.828-833.1999
Chuang MJ, Lai MC, Yang DR. Regulatory factors associated with synthesis of the osmolyte glycine betaine in the halophilic methanoarchaeon Methanohalophilus portucalensis. Appl Environ Microbiol. 1999 Feb;65(2):828-33. doi: 10.1128/AEM.65.2.828-833.1999. PMID: 9925623; PMCID: PMC91102.
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