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Volumn 29, Issue 12, 2008, Pages 2537-2539

One-pot synthesis of naphthalenes from baylis-hillman adducts via Pd-mediated successive allylation and arylation

Author keywords

Allylation; Arylation; Baylis Hillman adducts; Naphthalenes; Palladium

Indexed keywords


EID: 60149112765     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2008.29.12.2537     Document Type: Article
Times cited : (10)

References (41)
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    • For the general review on Baylis-Hillman reaction, see: Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811-891
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    • and further references cited therein
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    • For the Pd-mediated introduction of nucleophile at the primary position of Baylis-Hillman adducts, see
    • For the Pd-mediated introduction of nucleophile at the primary position of Baylis-Hillman adducts, see: Rajesh, S.; Banerji, B.; Iqbal, J. J. Org. Chem. 2002, 67, 7852-7857.
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    • 0037450980 scopus 로고    scopus 로고
    • For the Pd-mediated allylation of active methylene compounds, see
    • For the Pd-mediated allylation of active methylene compounds, see: Jousse-Karinthi, C.; Zouhiri, F.; Mahuteau, J.; Desmaele, D. Tetrahedron 2003, 59, 2093-2099.
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    • For our recent papers on the Pd-mediated reactions using the Baylis-Hillman adducts, see
    • For our recent papers on the Pd-mediated reactions using the Baylis-Hillman adducts, see: Gowrisankar, S.; Lee, H. S.; Kim, J. M.; Kim, J. N. Tetrahedron Lett. 2008, 49, 1670-1673.
    • (2008) Tetrahedron Lett. , vol.49 , pp. 1670-1673
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    • 0037189133 scopus 로고    scopus 로고
    • For the synthesis of naphthalenes from Baylis-Hillman adducts, see
    • For the synthesis of naphthalenes from Baylis-Hillman adducts, see: Im, Y. J.; Lee, K. Y.; Kim, T. H.; Kim, J. N. Tetrahedron Lett. 2002, 43, 4675-4678.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 4675-4678
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    • note
    • The reaction of 1a and 2a also produced 5a without Pd catalyst, however, the yield was lower (51%) and required long time (10 h) at higher temperature (110 °C). The explanation on the mechanism of the last step, dealkoxycarbonylation and concomitant aerobic oxidation, is not clear at this stage and needs further study.
  • 34
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    • For the introduction of active methylene compounds at the primary position of Baylis-Hillman adducts and their synthetic applications, see
    • For the introduction of active methylene compounds at the primary position of Baylis-Hillman adducts and their synthetic applications, see: Gowrisanakr, S.; Lee, H. S.; Kim, J. N. Bull. Korean Chem. Soc. 2006, 27, 2097-2100.
    • (2006) Bull. Korean Chem. Soc. , vol.27 , pp. 2097-2100
    • Gowrisanakr, S.1    Lee, H.S.2    Kim, J.N.3
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    • note
    • °C).
  • 37
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    • note
    • Compound 5a was also generated from 4a without the influence of Pd catalyst in a similar yield (63%). The results state that the last step is a base-mediated process not Pd-mediated one, actually.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.