DOI: 10.1002/ejoc.200400145. Sonogashira Cross‐Couplings of Dehydroamino Acid Derivatives and Phenylacetylenes

Sonogashira Cross‐Couplings of Dehydroamino Acid Derivatives and Phenylacetylenes

10.1002/ejoc.200400145

Crossref journal-article

Wiley

European Journal of Organic Chemistry (311)

Abstract

AbstractSeveral phenylacetylenes were coupled under Sonogashira cross‐coupling conditions with the methyl esters of N‐(tert‐butoxycarbonyl)‐(E)‐β‐bromo‐ or ‐β,β‐dibromodehydroalanine, to give β‐substituted or β,β‐disubstituted dehydroalanines, respectively. The β‐substituted dehydroalanines were obtained in good to high yields (60−90%) under the usual Sonogashira conditions (1 equiv. of the phenylacetylene, 1 mol % of [Pd(PPh3)4], 2 mol % of CuI, 18 equiv. of NEt3 in acetonitrile, 24 h at room temp.), with retention of stereochemistry. The β,β‐disubstituted dehydroalanines were, in turn, obtained in moderate to good yields (44−63%) under modified Sonogashira conditions (4 equiv. of the phenylacetylene,10 mol % of [PdCl2(PPh3)2], 20 mol % of CuI, 1.4 equiv. of Cs2CO3 in acetonitrile, 2 h at reflux). In the latter reactions, some phenylacetylene dimer and the (E) isomer of the monosubstituted coupled products were also isolated to some extent. The Sonogashira products obtained from the 4‐bromophenylacetylene were allowed to react with functionalized benzo[b]thiophenes under C−C or C−N palladium‐catalyzed cross‐coupling conditions. Preliminary fluorescence studies were performed for mono‐ and disubstituted (4‐aminophenyl)acetylenic dehydroamino acids and for the benzo[b]thiophene derivatives. The results showed that some of the dehydroalanines prepared can be used as fluorescent probes. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

Bibliography

Abreu, A. S., Ferreira, P. M. T., Queiroz, M. R. P., Gatto, E., & Venanzi, M. (2004). Sonogashira CrossâCouplings of Dehydroamino Acid Derivatives and Phenylacetylenes. European Journal of Organic Chemistry, 2004(19), 3985â3991. Portico.

Authors 5

Ana S. Abreu (first)
Paula M. T. Ferreira (additional)
Maria‐João R. P. Queiroz (additional)
Emanuela Gatto (additional)
Mariano Venanzi (additional)

References 14 Referenced 17

10.1002/ejoc.200300103
{'key': 'e_1_2_6_2_2', 'first-page': '1077', 'author': 'Stanovick B.', 'year': '2000', 'journal-title': 'Synlett'} / Synlett by Stanovick B. (2000)
J. Svete J. Heterocycl. Chem.2002 39 437−454 and references cited therein. (10.1002/jhet.5570390302)
10.1002/ejoc.200300394
10.1002/1099-0690(200208)2002:15<2524::AID-EJOC2524>3.0.CO;2-W
10.1002/ejoc.200390212
10.1016/S0040-4039(03)00564-1
10.1039/b001538p
10.1016/S0040-4020(97)10197-1
10.1021/ol034360d
10.1021/ol0162421
10.1016/S0022-328X(02)01158-0
10.1016/S0022-328X(02)01262-7
10.1021/cr940745l

Dates

Type	When
Created	20 years, 11 months ago (Sept. 16, 2004, 8:03 a.m.)
Deposited	2 years ago (Sept. 2, 2023, 11:27 p.m.)
Indexed	3 months, 4 weeks ago (May 9, 2025, 12:37 p.m.)
Issued	20 years, 11 months ago (Sept. 16, 2004)
Published	20 years, 11 months ago (Sept. 16, 2004)
Published Online	20 years, 11 months ago (Sept. 16, 2004)
Published Print	20 years, 11 months ago (Oct. 1, 2004)

Funders 0

None

BibTeX

@article{Abreu_2004, title={Sonogashira Cross‐Couplings of Dehydroamino Acid Derivatives and Phenylacetylenes}, volume={2004}, ISSN={1099-0690}, url={http://dx.doi.org/10.1002/ejoc.200400145}, DOI={10.1002/ejoc.200400145}, number={19}, journal={European Journal of Organic Chemistry}, publisher={Wiley}, author={Abreu, Ana S. and Ferreira, Paula M. T. and Queiroz, Maria‐João R. P. and Gatto, Emanuela and Venanzi, Mariano}, year={2004}, month=sep, pages={3985–3991} }

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