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Tandem cyclization of alkynes via rhodium alkynyl and alkenylidene catalysis.
J Am Chem Soc. 2006 Nov 22; 128(46):14818-9.JA

Abstract

A rhodium(I)-catalyzed tandem cyclization of alkynes has been developed. The reaction allows for multiple bond formations to occur at both the alpha- and beta-positions of alkynes under mild conditions to yield a variety of fused ring systems as the products. In the presence of triethylamine and the complex derived from [Rh(COD)Cl]2 and P(4-F-C6H4)3, a terminal alkyne is converted to a rhodium alkynyl species which reacts with a tethered alkyl halide at the beta-position to provide a beta,beta-disubstituted alkenylidene complex. The rhodium alkenylidene species then undergoes additional ring closures with a range of pendent functional groups such as alkene, hydroxyl, and phenyl groups through [2 + 2] cycloaddition, nucleophilic addition, and 6pi-electrocyclization processes, respectively.

Authors+Show Affiliations

Department of Chemistry, Princeton University, Princeton, NJ 08544, USA.No affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

Language

eng

PubMed ID

17105287

Citation

Joo, Jung Min, et al. "Tandem Cyclization of Alkynes Via Rhodium Alkynyl and Alkenylidene Catalysis." Journal of the American Chemical Society, vol. 128, no. 46, 2006, pp. 14818-9.
Joo JM, Yuan Y, Lee C. Tandem cyclization of alkynes via rhodium alkynyl and alkenylidene catalysis. J Am Chem Soc. 2006;128(46):14818-9.
Joo, J. M., Yuan, Y., & Lee, C. (2006). Tandem cyclization of alkynes via rhodium alkynyl and alkenylidene catalysis. Journal of the American Chemical Society, 128(46), 14818-9.
Joo JM, Yuan Y, Lee C. Tandem Cyclization of Alkynes Via Rhodium Alkynyl and Alkenylidene Catalysis. J Am Chem Soc. 2006 Nov 22;128(46):14818-9. PubMed PMID: 17105287.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Tandem cyclization of alkynes via rhodium alkynyl and alkenylidene catalysis. AU - Joo,Jung Min, AU - Yuan,Yu, AU - Lee,Chulbom, PY - 2006/11/16/pubmed PY - 2007/9/6/medline PY - 2006/11/16/entrez SP - 14818 EP - 9 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 128 IS - 46 N2 - A rhodium(I)-catalyzed tandem cyclization of alkynes has been developed. The reaction allows for multiple bond formations to occur at both the alpha- and beta-positions of alkynes under mild conditions to yield a variety of fused ring systems as the products. In the presence of triethylamine and the complex derived from [Rh(COD)Cl]2 and P(4-F-C6H4)3, a terminal alkyne is converted to a rhodium alkynyl species which reacts with a tethered alkyl halide at the beta-position to provide a beta,beta-disubstituted alkenylidene complex. The rhodium alkenylidene species then undergoes additional ring closures with a range of pendent functional groups such as alkene, hydroxyl, and phenyl groups through [2 + 2] cycloaddition, nucleophilic addition, and 6pi-electrocyclization processes, respectively. SN - 0002-7863 UR - https://www.unboundmedicine.com/medline/citation/17105287/Tandem_cyclization_of_alkynes_via_rhodium_alkynyl_and_alkenylidene_catalysis_ L2 - https://doi.org/10.1021/ja066374v DB - PRIME DP - Unbound Medicine ER -
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