DOI: 10.1002/adsc.200800666. Development of the First Iron Chloride‐Catalyzed Hydration of Terminal Alkynes

Development of the First Iron Chloride‐Catalyzed Hydration of Terminal Alkynes

10.1002/adsc.200800666

Crossref journal-article

Wiley

Advanced Synthesis & Catalysis (311)

Abstract

Abstractmagnified imageThe development of the first iron‐catalyzed hydration of terminal alkynes is described using a catalytic amount of iron(III) chloride (10 mol%). The reaction leads selectively to the corresponding methyl ketone derivatives.

Bibliography

Wu, X., Bezier, D., & Darcel, C. (2009). Development of the First Iron ChlorideâCatalyzed Hydration of Terminal Alkynes. Advanced Synthesis & Catalysis, 351(3), 367â370. Portico.

Authors 3

Xiao‐Feng Wu (first)
David Bezier (additional)
Christophe Darcel (additional)

References 46 Referenced 126

10.1055/s-2007-966002
{'key': 'e_1_2_2_2_2', 'first-page': '805', 'volume': '50', 'author': 'Berthelot M.', 'year': '1862', 'journal-title': 'C.\u2005R. Hebd. Seances Acad. Sci.'} / C. R. Hebd. Seances Acad. Sci. by Berthelot M. (1862)
{'key': 'e_1_2_2_3_2', 'first-page': '4', 'volume-title': 'Comprehensive Organic Synthesis', 'author': 'Larock R. C.', 'year': '1991'} / Comprehensive Organic Synthesis by Larock R. C. (1991)
{'key': 'e_1_2_2_4_2', 'first-page': '76', 'volume-title': 'Advanced Organic Chemistry', 'author': 'March J.', 'year': '1992'} / Advanced Organic Chemistry by March J. (1992)
10.1021/jo00011a058
10.1021/ja01480a036
10.1021/ja00974a020
10.1016/0304-5102(90)85019-E
10.1016/0304-5102(92)80117-Y
10.1021/om00157a005
10.1021/jo00078a056
10.1021/jo961740m
10.1016/0304-5102(93)87031-3
10.1016/S0040-4039(00)85408-8
10.1002/(SICI)1521-3757(19981016)110:20<3024::AID-ANGE3024>3.0.CO;2-0
10.1002/(SICI)1521-3773(19981102)37:20<2867::AID-ANIE2867>3.0.CO;2-E
10.1021/ol0003937
10.1016/S0040-4039(01)01841-X
10.1021/ja0119292
10.1002/1521-3757(20011015)113:20<4002::AID-ANGE4002>3.0.CO;2-R
10.1002/1521-3773(20011015)40:20<3884::AID-ANIE3884>3.0.CO;2-7
10.1021/ja046360u
10.1002/ange.200503826
10.1002/anie.200503826
10.1021/ol062455k
For complete reviews of the state of the art see:
10.1021/cr040664h
10.1002/ange.200800012
10.1002/anie.200800012
10.1039/b801794h
10.1016/0022-328X(96)06294-8
10.1021/jo048410j
{'key': 'e_1_2_2_29_2', 'first-page': '595', 'volume': '116', 'author': 'Bassetti M.', 'year': '1986', 'journal-title': 'Gazz. Chim. Ital.'} / Gazz. Chim. Ital. by Bassetti M. (1986)
In the palladium series see for examples:
{'key': 'e_1_2_2_31_2', 'first-page': '1998', 'author': 'Rothenberg G.', 'year': '2001', 'journal-title': 'J. Chem. Soc. Perkin Trans. 2'} / J. Chem. Soc. Perkin Trans. 2 by Rothenberg G. (2001)
10.1016/S1381-1169(97)00140-4
10.1016/0040-4039(95)00286-3
10.1021/ja00105a014
In the iron series see for examples:
10.1021/ol047509
10.1021/ol050340v
For examples of palladium‐catalyzed homocoupling with air as re‐oxidant see:
10.1021/jo9514329
10.1055/s-1997-710
{'key': 'e_1_2_2_41_2', 'first-page': '2351', 'author': 'Punna S.', 'year': '2004', 'journal-title': 'Synlett'} / Synlett by Punna S. (2004)
10.1016/S0022-328X(02)02153-8

Dates

Type	When
Created	16 years, 6 months ago (Feb. 17, 2009, 2:39 a.m.)
Deposited	1 year, 9 months ago (Nov. 13, 2023, 8:35 p.m.)
Indexed	1 month ago (Aug. 2, 2025, 12:59 a.m.)
Issued	16 years, 7 months ago (Feb. 1, 2009)
Published	16 years, 7 months ago (Feb. 1, 2009)
Published Online	16 years, 6 months ago (Feb. 17, 2009)
Published Print	16 years, 7 months ago (Feb. 1, 2009)

Funders 0

None

BibTeX

@article{Wu_2009, title={Development of the First Iron Chloride‐Catalyzed Hydration of Terminal Alkynes}, volume={351}, ISSN={1615-4169}, url={http://dx.doi.org/10.1002/adsc.200800666}, DOI={10.1002/adsc.200800666}, number={3}, journal={Advanced Synthesis & Catalysis}, publisher={Wiley}, author={Wu, Xiao‐Feng and Bezier, David and Darcel, Christophe}, year={2009}, month=feb, pages={367–370} }

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