DOI: 10.1002/adsc.200404063. Room Temperature Aerobic Copper–Catalysed Selective Oxidation of Primary Alcohols to Aldehydes

Room Temperature Aerobic Copper–Catalysed Selective Oxidation of Primary Alcohols to Aldehydes

10.1002/adsc.200404063

Crossref journal-article

Wiley

Advanced Synthesis & Catalysis (311)

Abstract

AbstractA novel and very mild method for the oxidation of primary alcohols to aldehydes with excellent conversions has been developed. The reaction is carried out under air at room temperature and is catalysed using a [copper(II)‐(N ligand)n] complex with TEMPO and a base as co‐catalysts. In this paper, the performance of a series of N‐containing ligands, as well as different copper(II) salt precursors in different solvents are reported. Best results are obtained in acetonitrile/water as solvent using a copper(II) catalyst generated in situ from a Cu(II) salt with weak or non‐coordinating anions and bipyridine ligands with electron‐donating substituents. A reaction mechanism is postulated which resembles that of galactose oxidase, and in which TEMPO seems to be involved as a hydrogen acceptor.

Bibliography

Gamez, P., Arends, I. W. C. E., Sheldon, R. A., & Reedijk, J. (2004). Room Temperature Aerobic CopperâCatalysed Selective Oxidation of Primary Alcohols to Aldehydes. Advanced Synthesis & Catalysis, 346(7), 805â811. Portico.

Authors 4

Patrick Gamez (first)
Isabel W. C. E. Arends (additional)
Roger A. Sheldon (additional)
Jan Reedijk (additional)

References 38 Referenced 330

{'key': 'e_1_2_1_1_2', 'volume-title': 'Metal‐Catalysed Oxidations of Organic Compounds', 'author': 'Sheldon R. A.', 'year': '1981'} / Metal‐Catalysed Oxidations of Organic Compounds by Sheldon R. A. (1981)
10.1055/s-1996-4369
10.1016/S0920-5861(99)00317-X
10.1016/0920-5861(94)80187-8
10.1039/B212585B
10.1007/978-3-642-69362-5
{'key': 'e_1_2_1_7_2', 'volume-title': 'Oxidation in Organic Chemistry', 'author': 'Trahanovsky W. S.', 'year': '1978'} / Oxidation in Organic Chemistry by Trahanovsky W. S. (1978)
10.1021/jo000760s
10.1039/a707339i
10.1021/ja973227b
10.1039/b209344h
10.1021/ja0282691
10.1016/S0040-4039(02)01678-7
{'key': 'e_1_2_1_14_2', 'volume-title': 'Bioinorganic Chemistry, An Introduction', 'author': 'Ochiai E.', 'year': '1977'} / Bioinorganic Chemistry, An Introduction by Ochiai E. (1977)
10.1039/b104827a
10.1021/ja00323a064
10.1016/S0040-4039(00)84193-3
10.1016/0920-5861(95)00186-7
10.1021/jo982239s
10.1126/science.274.5295.2044
10.1126/science.279.5350.537
10.1002/(SICI)1521-3773(19980904)37:16<2217::AID-ANIE2217>3.0.CO;2-D
10.1016/S0040-4020(02)00250-8
10.1016/S0040-4039(00)00620-1
10.1021/ol025721c
10.1002/ejoc.200300324
10.1039/b308668b
10.1039/b305941c
10.1021/ja00215a055
10.1021/ic00023a039
10.1016/S0014-3057(00)00259-7
10.1107/S0567740877005019
{'key': 'e_1_2_1_33_2', 'author': 'Willett R. D.', 'year': '1969', 'journal-title': 'Acta Crystallogr. A'} / Acta Crystallogr. A by Willett R. D. (1969)
10.1021/ja0103804
10.1021/ja9621354
10.1016/S0006-3495(93)81437-1
10.1021/ja00075a019
10.1016/S0021-9258(18)83205-7

Dates

Type	When
Created	21 years, 1 month ago (July 19, 2004, 7:11 a.m.)
Deposited	1 year, 9 months ago (Nov. 17, 2023, 2:28 a.m.)
Indexed	2 weeks, 1 day ago (Aug. 20, 2025, 9:17 a.m.)
Issued	21 years, 3 months ago (June 1, 2004)
Published	21 years, 3 months ago (June 1, 2004)
Published Online	21 years, 1 month ago (July 19, 2004)
Published Print	21 years, 3 months ago (June 1, 2004)

Funders 0

None

BibTeX

@article{Gamez_2004, title={Room Temperature Aerobic Copper–Catalysed Selective Oxidation of Primary Alcohols to Aldehydes}, volume={346}, ISSN={1615-4169}, url={http://dx.doi.org/10.1002/adsc.200404063}, DOI={10.1002/adsc.200404063}, number={7}, journal={Advanced Synthesis & Catalysis}, publisher={Wiley}, author={Gamez, Patrick and Arends, Isabel W. C. E. and Sheldon, Roger A. and Reedijk, Jan}, year={2004}, month=jun, pages={805–811} }

JSON

{
  "indexed": {
    "date-parts": [
      [
        2025,
        8,
        20
      ]
    ],
    "date-time": "2025-08-20T13:17:30Z",
    "timestamp": 1755695850903
  },
  "reference-count": 38,
  "publisher": "Wiley",
  "issue": "7",
  "license": [
    {
      "start": {
        "date-parts": [
          [
            2004,
            7,
            19
          ]
        ],
        "date-time": "2004-07-19T00:00:00Z",
        "timestamp": 1090195200000
      },
      "content-version": "vor",
      "delay-in-days": 48,
      "URL": "http://onlinelibrary.wiley.com/termsAndConditions#vor"
    }
  ],
  "content-domain": {
    "domain": [],
    "crossmark-restriction": false
  },
  "published-print": {
    "date-parts": [
      [
        2004,
        6
      ]
    ]
  },
  "abstract": "<jats:title>Abstract</jats:title><jats:p>A novel and very mild method for the oxidation of primary alcohols to aldehydes with excellent conversions has been developed. The reaction is carried out under air at room temperature and is catalysed using a [copper(II)\u2010(N ligand)<jats:sub>n</jats:sub>] complex with TEMPO and a base as co\u2010catalysts. In this paper, the performance of a series of N\u2010containing ligands, as well as different copper(II) salt precursors in different solvents are reported. Best results are obtained in acetonitrile/water as solvent using a copper(II) catalyst generated <jats:italic>in situ</jats:italic> from a Cu(II) salt with weak or non\u2010coordinating anions and bipyridine ligands with electron\u2010donating substituents. A reaction mechanism is postulated which resembles that of galactose oxidase, and in which TEMPO seems to be involved as a hydrogen acceptor.</jats:p>",
  "DOI": "10.1002/adsc.200404063",
  "type": "journal-article",
  "created": {
    "date-parts": [
      [
        2004,
        7,
        19
      ]
    ],
    "date-time": "2004-07-19T11:11:15Z",
    "timestamp": 1090235475000
  },
  "page": "805-811",
  "source": "Crossref",
  "is-referenced-by-count": 330,
  "title": "Room Temperature Aerobic Copper\u2013Catalysed Selective Oxidation of Primary Alcohols to Aldehydes",
  "prefix": "10.1002",
  "volume": "346",
  "author": [
    {
      "given": "Patrick",
      "family": "Gamez",
      "sequence": "first",
      "affiliation": []
    },
    {
      "given": "Isabel\u2005W.\u2005C.\u2005E.",
      "family": "Arends",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Roger\u2005A.",
      "family": "Sheldon",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Jan",
      "family": "Reedijk",
      "sequence": "additional",
      "affiliation": []
    }
  ],
  "member": "311",
  "published-online": {
    "date-parts": [
      [
        2004,
        7,
        19
      ]
    ]
  },
  "reference": [
    {
      "key": "e_1_2_1_1_2",
      "volume-title": "Metal\u2010Catalysed Oxidations of Organic Compounds",
      "author": "Sheldon R. A.",
      "year": "1981"
    },
    {
      "key": "e_1_2_1_2_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1055/s-1996-4369"
    },
    {
      "key": "e_1_2_1_3_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0920-5861(99)00317-X"
    },
    {
      "key": "e_1_2_1_4_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/0920-5861(94)80187-8"
    },
    {
      "key": "e_1_2_1_5_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1039/B212585B"
    },
    {
      "key": "e_1_2_1_6_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1007/978-3-642-69362-5"
    },
    {
      "key": "e_1_2_1_7_2",
      "volume-title": "Oxidation in Organic Chemistry",
      "author": "Trahanovsky W. S.",
      "year": "1978"
    },
    {
      "key": "e_1_2_1_8_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/jo000760s"
    },
    {
      "key": "e_1_2_1_9_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1039/a707339i"
    },
    {
      "key": "e_1_2_1_10_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja973227b"
    },
    {
      "key": "e_1_2_1_11_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1039/b209344h"
    },
    {
      "key": "e_1_2_1_12_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja0282691"
    },
    {
      "key": "e_1_2_1_13_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0040-4039(02)01678-7"
    },
    {
      "key": "e_1_2_1_14_2",
      "volume-title": "Bioinorganic Chemistry, An Introduction",
      "author": "Ochiai E.",
      "year": "1977"
    },
    {
      "key": "e_1_2_1_15_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1039/b104827a"
    },
    {
      "key": "e_1_2_1_16_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja00323a064"
    },
    {
      "key": "e_1_2_1_17_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0040-4039(00)84193-3"
    },
    {
      "key": "e_1_2_1_18_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/0920-5861(95)00186-7"
    },
    {
      "key": "e_1_2_1_19_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/jo982239s"
    },
    {
      "key": "e_1_2_1_20_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1126/science.274.5295.2044"
    },
    {
      "key": "e_1_2_1_21_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1126/science.279.5350.537"
    },
    {
      "key": "e_1_2_1_22_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/(SICI)1521-3773(19980904)37:16<2217::AID-ANIE2217>3.0.CO;2-D"
    },
    {
      "key": "e_1_2_1_23_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0040-4020(02)00250-8"
    },
    {
      "key": "e_1_2_1_24_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0040-4039(00)00620-1"
    },
    {
      "key": "e_1_2_1_25_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ol025721c"
    },
    {
      "key": "e_1_2_1_26_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/ejoc.200300324"
    },
    {
      "key": "e_1_2_1_27_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1039/b308668b"
    },
    {
      "key": "e_1_2_1_28_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1039/b305941c"
    },
    {
      "key": "e_1_2_1_29_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja00215a055"
    },
    {
      "key": "e_1_2_1_30_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ic00023a039"
    },
    {
      "key": "e_1_2_1_31_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0014-3057(00)00259-7"
    },
    {
      "key": "e_1_2_1_32_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1107/S0567740877005019"
    },
    {
      "key": "e_1_2_1_33_2",
      "author": "Willett R. D.",
      "year": "1969",
      "journal-title": "Acta Crystallogr. A"
    },
    {
      "key": "e_1_2_1_34_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja0103804"
    },
    {
      "key": "e_1_2_1_35_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja9621354"
    },
    {
      "key": "e_1_2_1_36_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0006-3495(93)81437-1"
    },
    {
      "key": "e_1_2_1_37_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja00075a019"
    },
    {
      "key": "e_1_2_1_38_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0021-9258(18)83205-7"
    }
  ],
  "container-title": "Advanced Synthesis &amp; Catalysis",
  "original-title": [],
  "language": "en",
  "link": [
    {
      "URL": "https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fadsc.200404063",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "text-mining"
    },
    {
      "URL": "https://onlinelibrary.wiley.com/doi/pdf/10.1002/adsc.200404063",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "similarity-checking"
    }
  ],
  "deposited": {
    "date-parts": [
      [
        2023,
        11,
        17
      ]
    ],
    "date-time": "2023-11-17T07:28:32Z",
    "timestamp": 1700206112000
  },
  "score": 1,
  "resource": {
    "primary": {
      "URL": "https://onlinelibrary.wiley.com/doi/10.1002/adsc.200404063"
    }
  },
  "subtitle": [],
  "short-title": [],
  "issued": {
    "date-parts": [
      [
        2004,
        6
      ]
    ]
  },
  "references-count": 38,
  "journal-issue": {
    "issue": "7",
    "published-print": {
      "date-parts": [
        [
          2004,
          6
        ]
      ]
    }
  },
  "alternative-id": [
    "10.1002/adsc.200404063"
  ],
  "URL": "http://dx.doi.org/10.1002/adsc.200404063",
  "relation": {},
  "ISSN": [
    "1615-4150",
    "1615-4169"
  ],
  "subject": [],
  "container-title-short": "Adv Synth Catal",
  "published": {
    "date-parts": [
      [
        2004,
        6
      ]
    ]
  }
}