DOI: 10.1002/cssc.200800019. High‐Surface‐Area TiO<sub>2</sub> and TiN as Catalysts for the CC Coupling of Alcohols and Ketones

High‐Surface‐Area TiO2 and TiN as Catalysts for the CC Coupling of Alcohols and Ketones

10.1002/cssc.200800019

Crossref journal-article

Wiley

ChemSusChem (311)

Abstract

AbstractTo design more sustainable processes for the alkylation of ketones, the use of both atom‐ineffective leaving groups such as halides and boron as well as noble‐metal‐based catalysts should be avoided. For that purpose, high‐surface‐area titanium nitride was prepared from high‐surface‐area titanium dioxide using cyanamide as a transcription agent. The resulting nitride as well as the initial oxide proved to be effective and versatile catalysts for the alkylation of ketones with alcohols. Interestingly, the TiN catalyst yields unsaturated compounds, while the oxide‐based catalyst mainly yields saturated coupling products. As a result of its metallic properties, TiN shows a strong tendency to catalyse the dehydrogenation of alcohols, which then undergo aldol condensation with ketones. In contrast, TiO2 promotes the direct nucleophilic attack of ketones on alcohols.

Bibliography

Fischer, A., Makowski, P., MÃ¼ller, J., Antonietti, M., Thomas, A., & Goettmann, F. (2008). HighâSurfaceâArea TiO2 and TiN as Catalysts for the Cï£¿C Coupling of Alcohols and Ketones. ChemSusChem, 1(5), 444â449. Portico.

Authors 6

Anna Fischer (first)
Philippe Makowski (additional)
Jens‐Oliver Müller (additional)
Markus Antonietti (additional)
Arne Thomas (additional)
Frederic Goettmann (additional)

References 38 Referenced 77

10.1002/ange.200400650
10.1002/anie.200400650
10.1002/(SICI)1099-0682(199907)1999:7<1047::AID-EJIC1047>3.0.CO;2-B
10.1002/adsc.200303094
10.1016/S0022-328X(98)01088-2
10.1002/ange.200502422
10.1002/anie.200502422
10.1016/j.tetlet.2006.07.069
10.1002/ange.200503263
10.1002/anie.200503263
P. Makowski R. Rothe M. Niederberger F. Goettmann unpublished results.
10.1002/ange.200603794
10.1002/anie.200603794
10.1021/j100096a017
10.1016/j.apcata.2005.01.029
10.1016/S1381-1169(03)00545-4
10.1021/ja0357689
10.1039/B608532F
10.1002/ange.200600412
10.1002/anie.200600412
10.1039/b618555j
10.1002/ange.200603478
10.1002/anie.200603478
10.1002/adma.200602151
10.1021/cm0701759
10.1016/j.mseb.2006.07.026
10.1016/j.jallcom.2005.04.197
Traces of rutile found in a small number of samples can be attributed to oxidation of TiN by air for those samples that are removed from the nitrogen atmosphere before they are carefully cooled down to room temperature.
10.1107/S0021889877012898
10.1039/b409143b
10.1002/adsc.200606192
{'key': 'e_1_2_6_26_2', 'first-page': '1627', 'volume': '10', 'author': 'Figueras F.', 'year': '2006', 'journal-title': 'Curr. Opin. Chem. Biol.'} / Curr. Opin. Chem. Biol. by Figueras F. (2006)
10.1002/chem.200500542
10.1039/b512543j
10.1021/cm0111534
10.1002/ange.200390040
10.1002/anie.200390072
10.1002/chem.200501152

Dates

Type	When
Created	17 years, 5 months ago (April 2, 2008, 10:29 a.m.)
Deposited	1 year, 10 months ago (Oct. 11, 2023, 12:30 a.m.)
Indexed	1 year, 2 months ago (June 25, 2024, 1:56 a.m.)
Issued	17 years, 3 months ago (May 15, 2008)
Published	17 years, 3 months ago (May 15, 2008)
Published Online	17 years, 3 months ago (May 15, 2008)
Published Print	17 years, 3 months ago (May 23, 2008)

Funders 0

None

BibTeX

@article{Fischer_2008, title={High‐Surface‐Area TiO2 and TiN as Catalysts for the CC Coupling of Alcohols and Ketones}, volume={1}, ISSN={1864-564X}, url={http://dx.doi.org/10.1002/cssc.200800019}, DOI={10.1002/cssc.200800019}, number={5}, journal={ChemSusChem}, publisher={Wiley}, author={Fischer, Anna and Makowski, Philippe and Müller, Jens‐Oliver and Antonietti, Markus and Thomas, Arne and Goettmann, Frederic}, year={2008}, month=may, pages={444–449} }

JSON

{
  "indexed": {
    "date-parts": [
      [
        2024,
        6,
        25
      ]
    ],
    "date-time": "2024-06-25T05:56:18Z",
    "timestamp": 1719294978385
  },
  "reference-count": 38,
  "publisher": "Wiley",
  "issue": "5",
  "license": [
    {
      "start": {
        "date-parts": [
          [
            2008,
            4,
            2
          ]
        ],
        "date-time": "2008-04-02T00:00:00Z",
        "timestamp": 1207094400000
      },
      "content-version": "vor",
      "delay-in-days": 0,
      "URL": "http://onlinelibrary.wiley.com/termsAndConditions#vor"
    }
  ],
  "content-domain": {
    "domain": [
      "chemistry-europe.onlinelibrary.wiley.com"
    ],
    "crossmark-restriction": true
  },
  "published-print": {
    "date-parts": [
      [
        2008,
        5,
        23
      ]
    ]
  },
  "abstract": "<jats:title>Abstract</jats:title><jats:p><jats:italic>To design more sustainable processes for the alkylation of ketones, the use of both atom\u2010ineffective leaving groups such as halides and boron as well as noble\u2010metal\u2010based catalysts should be avoided. For that purpose, high\u2010surface\u2010area titanium nitride was prepared from high\u2010surface\u2010area titanium dioxide using cyanamide as a transcription agent. The resulting nitride as well as the initial oxide proved to be effective and versatile catalysts for the alkylation of ketones with alcohols. Interestingly, the TiN catalyst yields unsaturated compounds, while the oxide\u2010based catalyst mainly yields saturated coupling products. As a result of its metallic properties, TiN shows a strong tendency to catalyse the dehydrogenation of alcohols, which then undergo aldol condensation with ketones. In contrast, TiO<jats:sub>2</jats:sub> promotes the direct nucleophilic attack of ketones on alcohols.</jats:italic></jats:p>",
  "DOI": "10.1002/cssc.200800019",
  "type": "journal-article",
  "created": {
    "date-parts": [
      [
        2008,
        4,
        2
      ]
    ],
    "date-time": "2008-04-02T14:29:12Z",
    "timestamp": 1207146552000
  },
  "page": "444-449",
  "update-policy": "http://dx.doi.org/10.1002/crossmark_policy",
  "source": "Crossref",
  "is-referenced-by-count": 77,
  "title": "High\u2010Surface\u2010Area TiO<sub>2</sub> and TiN as Catalysts for the C\uf8ffC Coupling of Alcohols and Ketones",
  "prefix": "10.1002",
  "volume": "1",
  "author": [
    {
      "given": "Anna",
      "family": "Fischer",
      "sequence": "first",
      "affiliation": []
    },
    {
      "given": "Philippe",
      "family": "Makowski",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Jens\u2010Oliver",
      "family": "M\u00fcller",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Markus",
      "family": "Antonietti",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Arne",
      "family": "Thomas",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Frederic",
      "family": "Goettmann",
      "sequence": "additional",
      "affiliation": []
    }
  ],
  "member": "311",
  "published-online": {
    "date-parts": [
      [
        2008,
        5,
        15
      ]
    ]
  },
  "reference": [
    {
      "key": "e_1_2_6_1_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/ange.200400650"
    },
    {
      "key": "e_1_2_6_1_3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/anie.200400650"
    },
    {
      "key": "e_1_2_6_2_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/(SICI)1099-0682(199907)1999:7<1047::AID-EJIC1047>3.0.CO;2-B"
    },
    {
      "key": "e_1_2_6_3_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/adsc.200303094"
    },
    {
      "key": "e_1_2_6_4_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0022-328X(98)01088-2"
    },
    {
      "key": "e_1_2_6_5_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/ange.200502422"
    },
    {
      "key": "e_1_2_6_5_3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/anie.200502422"
    },
    {
      "key": "e_1_2_6_6_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/j.tetlet.2006.07.069"
    },
    {
      "key": "e_1_2_6_7_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/ange.200503263"
    },
    {
      "key": "e_1_2_6_7_3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/anie.200503263"
    },
    {
      "key": "e_1_2_6_8_2",
      "unstructured": "P. Makowski R. Rothe M. Niederberger F. Goettmann unpublished results."
    },
    {
      "key": "e_1_2_6_9_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/ange.200603794"
    },
    {
      "key": "e_1_2_6_9_3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/anie.200603794"
    },
    {
      "key": "e_1_2_6_10_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/j100096a017"
    },
    {
      "key": "e_1_2_6_11_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/j.apcata.2005.01.029"
    },
    {
      "key": "e_1_2_6_12_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S1381-1169(03)00545-4"
    },
    {
      "key": "e_1_2_6_13_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja0357689"
    },
    {
      "key": "e_1_2_6_14_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1039/B608532F"
    },
    {
      "key": "e_1_2_6_15_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/ange.200600412"
    },
    {
      "key": "e_1_2_6_15_3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/anie.200600412"
    },
    {
      "key": "e_1_2_6_16_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1039/b618555j"
    },
    {
      "key": "e_1_2_6_17_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/ange.200603478"
    },
    {
      "key": "e_1_2_6_17_3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/anie.200603478"
    },
    {
      "key": "e_1_2_6_18_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/adma.200602151"
    },
    {
      "key": "e_1_2_6_19_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/cm0701759"
    },
    {
      "key": "e_1_2_6_20_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/j.mseb.2006.07.026"
    },
    {
      "key": "e_1_2_6_21_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/j.jallcom.2005.04.197"
    },
    {
      "key": "e_1_2_6_22_2",
      "unstructured": "Traces of rutile found in a small number of samples can be attributed to oxidation of TiN by air for those samples that are removed from the nitrogen atmosphere before they are carefully cooled down to room temperature."
    },
    {
      "key": "e_1_2_6_23_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1107/S0021889877012898"
    },
    {
      "key": "e_1_2_6_24_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1039/b409143b"
    },
    {
      "key": "e_1_2_6_25_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/adsc.200606192"
    },
    {
      "key": "e_1_2_6_26_2",
      "first-page": "1627",
      "volume": "10",
      "author": "Figueras F.",
      "year": "2006",
      "journal-title": "Curr. Opin. Chem. Biol."
    },
    {
      "key": "e_1_2_6_27_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/chem.200500542"
    },
    {
      "key": "e_1_2_6_28_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1039/b512543j"
    },
    {
      "key": "e_1_2_6_29_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/cm0111534"
    },
    {
      "key": "e_1_2_6_30_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/ange.200390040"
    },
    {
      "key": "e_1_2_6_30_3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/anie.200390072"
    },
    {
      "key": "e_1_2_6_31_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/chem.200501152"
    }
  ],
  "container-title": "ChemSusChem",
  "original-title": [],
  "language": "en",
  "link": [
    {
      "URL": "https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fcssc.200800019",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "text-mining"
    },
    {
      "URL": "https://onlinelibrary.wiley.com/doi/full/10.1002/cssc.200800019",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "similarity-checking"
    }
  ],
  "deposited": {
    "date-parts": [
      [
        2023,
        10,
        11
      ]
    ],
    "date-time": "2023-10-11T04:30:41Z",
    "timestamp": 1696998641000
  },
  "score": 1,
  "resource": {
    "primary": {
      "URL": "https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cssc.200800019"
    }
  },
  "subtitle": [],
  "short-title": [],
  "issued": {
    "date-parts": [
      [
        2008,
        5,
        15
      ]
    ]
  },
  "references-count": 38,
  "journal-issue": {
    "issue": "5",
    "published-print": {
      "date-parts": [
        [
          2008,
          5,
          23
        ]
      ]
    }
  },
  "alternative-id": [
    "10.1002/cssc.200800019"
  ],
  "URL": "http://dx.doi.org/10.1002/cssc.200800019",
  "relation": {},
  "ISSN": [
    "1864-5631",
    "1864-564X"
  ],
  "subject": [],
  "container-title-short": "ChemSusChem",
  "published": {
    "date-parts": [
      [
        2008,
        5,
        15
      ]
    ]
  },
  "assertion": [
    {
      "value": "2007-07-27",
      "order": 0,
      "name": "received",
      "label": "Received",
      "group": {
        "name": "publication_history",
        "label": "Publication History"
      }
    },
    {
      "value": "2008-05-15",
      "order": 2,
      "name": "published",
      "label": "Published",
      "group": {
        "name": "publication_history",
        "label": "Publication History"
      }
    }
  ]
}