DOI: 10.1246/bcsj.76.2399. Copper-Catalyzed Oxidation of Amines with Molecular Oxygen

Copper-Catalyzed Oxidation of Amines with Molecular Oxygen

10.1246/bcsj.76.2399

Crossref journal-article

Oxford University Press (OUP)

Bulletin of the Chemical Society of Japan (286)

Abstract

Abstract An improved system for selective aerobic oxidation of amines to imines or nitriles is presented. It involves commercially available and inexpensive copper(I) or (II) chloride as catalyst, toluene as solvent, and MS3A as dehydrating agent under an atmospheric pressure of oxygen. A variety of amines can be used as substrates for this oxidation system to give the corresponding nitriles from primary amines (up to 97% yield; TON, up to 60) and the imines from secondary amines (up to 90% yield; TON, up to 45).

Bibliography

Maeda, Y., Nishimura, T., & Uemura, S. (2003). Copper-Catalyzed Oxidation of Amines with Molecular Oxygen. Bulletin of the Chemical Society of Japan, 76(12), 2399â2403.

Authors 3

Yasunari Maeda (first)
Takahiro Nishimura (additional)
Sakae Uemura (additional)

References 46 Referenced 123

{'key': '2024012017480931500_r1'}
{'key': '2024012017480931500_r2'}
10.1039/b000153h
10.1016/S0920-5861(99)00222-9
10.1248/cpb.11.296
10.1016/S0040-4039(00)89979-7
{'key': '2024012017480931500_r7'}
10.1016/S0040-4039(00)70751-9
10.1016/0040-4020(73)80088-2
10.1021/jo00870a021
{'key': '2024012017480931500_r11'}
{'key': '2024012017480931500_r12'}
{'key': '2024012017480931500_r13'}
{'key': '2024012017480931500_r14'}
{'key': '2024012017480931500_r15'}
{'key': '2024012017480931500_r16'}
{'key': '2024012017480931500_r17'}
{'key': '2024012017480931500_r18'}
10.1139/v00-181
{'key': '2024012017480931500_r20'}
{'key': '2024012017480931500_r21'}
{'key': '2024012017480931500_r22'}
10.1016/0304-5102(82)80023-0
10.1016/0304-5102(89)80289-5
{'key': '2024012017480931500_r25'}
{'key': '2024012017480931500_r26'}
{'key': '2024012017480931500_r27'}
10.1002/anie.200250779
{'key': '2024012017480931500_r29'}
10.1016/S0040-4020(01)88376-9
10.1016/S0040-4039(00)89050-4
{'key': '2024012017480931500_r32'}
10.1016/S0040-4039(98)01235-0
10.1021/jo9906734
{'key': '2024012017480931500_r35'}
{'key': '2024012017480931500_r36'}
10.1246/bcsj.74.165
10.1021/jo010338r
10.1016/S0040-4039(01)01949-9
10.1021/jo025918i
{'key': '2024012017480931500_r41'}
10.1016/S0040-4039(00)80431-1
10.3987/COM-94-6991
{'key': '2024012017480931500_r44'}
10.1002/recl.19630820803
10.1246/bcsj.40.912

Dates

Type	When
Created	21 years, 8 months ago (Dec. 15, 2003, 1:02 a.m.)
Deposited	1 year, 7 months ago (Jan. 20, 2024, 12:48 p.m.)
Indexed	1 week, 3 days ago (Aug. 28, 2025, 8:41 a.m.)
Issued	21 years, 9 months ago (Dec. 1, 2003)
Published	21 years, 9 months ago (Dec. 1, 2003)
Published Online	21 years, 8 months ago (Dec. 15, 2003)
Published Print	21 years, 9 months ago (Dec. 1, 2003)

Funders 0

None

BibTeX

@article{Maeda_2003, title={Copper-Catalyzed Oxidation of Amines with Molecular Oxygen}, volume={76}, ISSN={1348-0634}, url={http://dx.doi.org/10.1246/bcsj.76.2399}, DOI={10.1246/bcsj.76.2399}, number={12}, journal={Bulletin of the Chemical Society of Japan}, publisher={Oxford University Press (OUP)}, author={Maeda, Yasunari and Nishimura, Takahiro and Uemura, Sakae}, year={2003}, month=dec, pages={2399–2403} }

JSON

{
  "indexed": {
    "date-parts": [
      [
        2025,
        8,
        28
      ]
    ],
    "date-time": "2025-08-28T12:41:16Z",
    "timestamp": 1756384876640
  },
  "reference-count": 46,
  "publisher": "Oxford University Press (OUP)",
  "issue": "12",
  "license": [
    {
      "start": {
        "date-parts": [
          [
            2003,
            12,
            1
          ]
        ],
        "date-time": "2003-12-01T00:00:00Z",
        "timestamp": 1070236800000
      },
      "content-version": "vor",
      "delay-in-days": 0,
      "URL": "https://academic.oup.com/pages/standard-publication-reuse-rights"
    }
  ],
  "content-domain": {
    "domain": [],
    "crossmark-restriction": false
  },
  "published-print": {
    "date-parts": [
      [
        2003,
        12,
        1
      ]
    ]
  },
  "abstract": "<jats:title>Abstract</jats:title>\n               <jats:p>An improved system for selective aerobic oxidation of amines to imines or nitriles is presented. It involves commercially available and inexpensive copper(I) or (II) chloride as catalyst, toluene as solvent, and MS3A as dehydrating agent under an atmospheric pressure of oxygen. A variety of amines can be used as substrates for this oxidation system to give the corresponding nitriles from primary amines (up to 97% yield; TON, up to 60) and the imines from secondary amines (up to 90% yield; TON, up to 45).</jats:p>",
  "DOI": "10.1246/bcsj.76.2399",
  "type": "journal-article",
  "created": {
    "date-parts": [
      [
        2003,
        12,
        15
      ]
    ],
    "date-time": "2003-12-15T06:02:06Z",
    "timestamp": 1071468126000
  },
  "page": "2399-2403",
  "source": "Crossref",
  "is-referenced-by-count": 123,
  "title": "Copper-Catalyzed Oxidation of Amines with Molecular Oxygen",
  "prefix": "10.1093",
  "volume": "76",
  "author": [
    {
      "given": "Yasunari",
      "family": "Maeda",
      "sequence": "first",
      "affiliation": [
        {
          "name": "Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto UniversitySakyo-ku, Kyoto 606-8501"
        }
      ]
    },
    {
      "given": "Takahiro",
      "family": "Nishimura",
      "sequence": "additional",
      "affiliation": [
        {
          "name": "Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto UniversitySakyo-ku, Kyoto 606-8501"
        }
      ]
    },
    {
      "given": "Sakae",
      "family": "Uemura",
      "sequence": "additional",
      "affiliation": [
        {
          "name": "Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto UniversitySakyo-ku, Kyoto 606-8501"
        }
      ]
    }
  ],
  "member": "286",
  "published-online": {
    "date-parts": [
      [
        2003,
        12,
        15
      ]
    ]
  },
  "reference": [
    {
      "key": "2024012017480931500_r1"
    },
    {
      "key": "2024012017480931500_r2"
    },
    {
      "key": "2024012017480931500_r3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1039/b000153h"
    },
    {
      "key": "2024012017480931500_r4",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0920-5861(99)00222-9"
    },
    {
      "key": "2024012017480931500_r5",
      "doi-asserted-by": "publisher",
      "DOI": "10.1248/cpb.11.296"
    },
    {
      "key": "2024012017480931500_r6",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0040-4039(00)89979-7"
    },
    {
      "key": "2024012017480931500_r7"
    },
    {
      "key": "2024012017480931500_r8",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0040-4039(00)70751-9"
    },
    {
      "key": "2024012017480931500_r9",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/0040-4020(73)80088-2"
    },
    {
      "key": "2024012017480931500_r10",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/jo00870a021"
    },
    {
      "key": "2024012017480931500_r11"
    },
    {
      "key": "2024012017480931500_r12"
    },
    {
      "key": "2024012017480931500_r13"
    },
    {
      "key": "2024012017480931500_r14"
    },
    {
      "key": "2024012017480931500_r15"
    },
    {
      "key": "2024012017480931500_r16"
    },
    {
      "key": "2024012017480931500_r17"
    },
    {
      "key": "2024012017480931500_r18"
    },
    {
      "key": "2024012017480931500_r19",
      "doi-asserted-by": "publisher",
      "DOI": "10.1139/v00-181"
    },
    {
      "key": "2024012017480931500_r20"
    },
    {
      "key": "2024012017480931500_r21"
    },
    {
      "key": "2024012017480931500_r22"
    },
    {
      "key": "2024012017480931500_r23",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/0304-5102(82)80023-0"
    },
    {
      "key": "2024012017480931500_r24",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/0304-5102(89)80289-5"
    },
    {
      "key": "2024012017480931500_r25"
    },
    {
      "key": "2024012017480931500_r26"
    },
    {
      "key": "2024012017480931500_r27"
    },
    {
      "key": "2024012017480931500_r28",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/anie.200250779"
    },
    {
      "key": "2024012017480931500_r29"
    },
    {
      "key": "2024012017480931500_r30",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0040-4020(01)88376-9"
    },
    {
      "key": "2024012017480931500_r31",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0040-4039(00)89050-4"
    },
    {
      "key": "2024012017480931500_r32"
    },
    {
      "key": "2024012017480931500_r33",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0040-4039(98)01235-0"
    },
    {
      "key": "2024012017480931500_r34",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/jo9906734"
    },
    {
      "key": "2024012017480931500_r35"
    },
    {
      "key": "2024012017480931500_r36"
    },
    {
      "key": "2024012017480931500_r37",
      "doi-asserted-by": "publisher",
      "DOI": "10.1246/bcsj.74.165"
    },
    {
      "key": "2024012017480931500_r38",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/jo010338r"
    },
    {
      "key": "2024012017480931500_r39",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0040-4039(01)01949-9"
    },
    {
      "key": "2024012017480931500_r40",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/jo025918i"
    },
    {
      "key": "2024012017480931500_r41"
    },
    {
      "key": "2024012017480931500_r42",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0040-4039(00)80431-1"
    },
    {
      "key": "2024012017480931500_r43",
      "doi-asserted-by": "publisher",
      "DOI": "10.3987/COM-94-6991"
    },
    {
      "key": "2024012017480931500_r44"
    },
    {
      "key": "2024012017480931500_r45",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/recl.19630820803"
    },
    {
      "key": "2024012017480931500_r46",
      "doi-asserted-by": "publisher",
      "DOI": "10.1246/bcsj.40.912"
    }
  ],
  "container-title": "Bulletin of the Chemical Society of Japan",
  "original-title": [],
  "language": "en",
  "link": [
    {
      "URL": "https://academic.oup.com/bcsj/article-pdf/76/12/2399/56264232/bcsj.76.2399.pdf",
      "content-type": "application/pdf",
      "content-version": "vor",
      "intended-application": "syndication"
    },
    {
      "URL": "https://academic.oup.com/bcsj/article-pdf/76/12/2399/56264232/bcsj.76.2399.pdf",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "similarity-checking"
    }
  ],
  "deposited": {
    "date-parts": [
      [
        2024,
        1,
        20
      ]
    ],
    "date-time": "2024-01-20T17:48:22Z",
    "timestamp": 1705772902000
  },
  "score": 1,
  "resource": {
    "primary": {
      "URL": "https://academic.oup.com/bcsj/article/76/12/2399/7340135"
    }
  },
  "subtitle": [],
  "short-title": [],
  "issued": {
    "date-parts": [
      [
        2003,
        12,
        1
      ]
    ]
  },
  "references-count": 46,
  "journal-issue": {
    "issue": "12",
    "published-online": {
      "date-parts": [
        [
          2003,
          12,
          15
        ]
      ]
    },
    "published-print": {
      "date-parts": [
        [
          2003,
          12,
          1
        ]
      ]
    }
  },
  "URL": "http://dx.doi.org/10.1246/bcsj.76.2399",
  "relation": {},
  "ISSN": [
    "0009-2673",
    "1348-0634"
  ],
  "subject": [],
  "published-other": {
    "date-parts": [
      [
        2003,
        12
      ]
    ]
  },
  "published": {
    "date-parts": [
      [
        2003,
        12,
        1
      ]
    ]
  }
}