DOI: 10.1246/cl.1995.681. Catalytic Addition of Aromatic C

Catalytic Addition of Aromatic C–H Bonds to Acetylenes

10.1246/cl.1995.681

Crossref journal-article

Oxford University Press (OUP)

Chemistry Letters (286)

Abstract

Abstract The reaction of α-tetralone with various internal acetylenes can be catalyzed by Ru(H)2(CO)(PPh3)3 and gives 1:1 addition products. Symmetrically substituted dialkyl- and diarylacetylenes gave an E/Z mixture of 1:1 coupling products in good yields. 1-Phenyl-1-butyne afforded all four possible regio- and stereoisomers. 1-Trimethylsilyl-1-propyne gave only E-isomer with C–C bond formation exclusively at the carbon atom substituted with the silyl group. Other internal acetylenes having a trimethylsilyl group also proceeded regioselectively although mixtures of stereoisomers were obtained.

Bibliography

Kakiuchi, F., Yamamoto, Y., Chatani, N., & Murai, S. (1995). Catalytic Addition of Aromatic CâH Bonds to Acetylenes. Chemistry Letters, 24(8), 681â682.

Authors 4

Fumitoshi Kakiuchi (first)
Yoshimi Yamamoto (additional)
Naoto Chatani (additional)
Shinji Murai (additional)

References 36 Referenced 166

10.1038/366529a0
10.1351/pac199466071527
10.1246/bcsj.68.62
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{'key': '2024011819345568300_r5'}
{'key': '2024011819345568300_r6'}
{'key': '2024011819345568300_r7'}
10.1016/0304-5102(89)80194-4
10.1021/om00049a045
{'key': '2024011819345568300_r10'}
{'key': '2024011819345568300_r11'}
10.1021/ja00025a027
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{'key': '2024011819345568300_r15'}
10.1021/cr00002a005
{'key': '2024011819345568300_r17'}
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{'key': '2024011819345568300_r19'}
10.1002/anie.198307161
10.1021/om00030a036
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{'key': '2024011819345568300_r24'}
10.1021/ja00040a015
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10.1021/ja00092a098
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Dates

Type	When
Created	19 years, 5 months ago (Feb. 28, 2006, 8:23 p.m.)
Deposited	1 year, 7 months ago (Jan. 18, 2024, 9:41 a.m.)
Indexed	1 day, 16 hours ago (Aug. 23, 2025, 1:02 a.m.)
Issued	30 years ago (Aug. 1, 1995)
Published	30 years ago (Aug. 1, 1995)
Published Online	19 years, 5 months ago (March 1, 2006)
Published Print	30 years ago (Aug. 1, 1995)

Funders 0

None

BibTeX

@article{Kakiuchi_1995, title={Catalytic Addition of Aromatic C–H Bonds to Acetylenes}, volume={24}, ISSN={1348-0715}, url={http://dx.doi.org/10.1246/cl.1995.681}, DOI={10.1246/cl.1995.681}, number={8}, journal={Chemistry Letters}, publisher={Oxford University Press (OUP)}, author={Kakiuchi, Fumitoshi and Yamamoto, Yoshimi and Chatani, Naoto and Murai, Shinji}, year={1995}, month=aug, pages={681–682} }

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