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Convenient one-pot synthesis of (E)-beta-aryl vinyl halides from benzyl bromides and dihalomethanes.
Org Lett. 2008 Dec 04; 10(23):5485-8.OL

Abstract

(E)-beta-aryl vinyl iodides are synthesized in high yield with excellent stereoselectivity from benzyl bromides by a one-pot homologation/stereoselective elimination procedure. Convenient conditions involving the anion of diiodomethane and an excess of base provide complete consumption of the benzyl bromide and elimination from a diiodoalkane intermediate. Similar conditions provide (E)-beta-aryl vinyl chlorides and bromides by employing the anions of ICH(2)Cl or CH(2)Br(2). The functional group tolerance and facile purification allows rapid access to a wide range of functionalized vinyl halides.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Bull JA
Department of Chemistry, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, Quebec, Canada H3C 3J7.
Mousseau JJ
No affiliation info available
Charette AB
No affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

18975954

Citation

Bull, James A., et al. "Convenient One-pot Synthesis of (E)-beta-aryl Vinyl Halides From Benzyl Bromides and Dihalomethanes." Organic Letters, vol. 10, no. 23, 2008, pp. 5485-8.
Bull JA, Mousseau JJ, Charette AB. Convenient one-pot synthesis of (E)-beta-aryl vinyl halides from benzyl bromides and dihalomethanes. Org Lett. 2008;10(23):5485-8.
Bull, J. A., Mousseau, J. J., & Charette, A. B. (2008). Convenient one-pot synthesis of (E)-beta-aryl vinyl halides from benzyl bromides and dihalomethanes. Organic Letters, 10(23), 5485-8. https://doi.org/10.1021/ol802315k
Bull JA, Mousseau JJ, Charette AB. Convenient One-pot Synthesis of (E)-beta-aryl Vinyl Halides From Benzyl Bromides and Dihalomethanes. Org Lett. 2008 Dec 4;10(23):5485-8. PubMed PMID: 18975954.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Convenient one-pot synthesis of (E)-beta-aryl vinyl halides from benzyl bromides and dihalomethanes. AU - Bull,James A, AU - Mousseau,James J, AU - Charette,André B, PY - 2008/11/4/pubmed PY - 2008/11/4/medline PY - 2008/11/4/entrez SP - 5485 EP - 8 JF - Organic letters JO - Org Lett VL - 10 IS - 23 N2 - (E)-beta-aryl vinyl iodides are synthesized in high yield with excellent stereoselectivity from benzyl bromides by a one-pot homologation/stereoselective elimination procedure. Convenient conditions involving the anion of diiodomethane and an excess of base provide complete consumption of the benzyl bromide and elimination from a diiodoalkane intermediate. Similar conditions provide (E)-beta-aryl vinyl chlorides and bromides by employing the anions of ICH(2)Cl or CH(2)Br(2). The functional group tolerance and facile purification allows rapid access to a wide range of functionalized vinyl halides. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/18975954/Convenient_one_pot_synthesis_of__E__beta_aryl_vinyl_halides_from_benzyl_bromides_and_dihalomethanes_ L2 - https://doi.org/10.1021/ol802315k DB - PRIME DP - Unbound Medicine ER -