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Rhodium-catalyzed addition of alkynes to activated ketones and aldehydes.
Org Lett. 2006 Jan 05; 8(1):67-9.OL

Abstract

[reaction: see text] The rhodium-catalyzed addition of alkynes to 1,2-diketones, 1,2-ketoesters, and aldehydes provides a method for the synthesis of tertiary alkynyl alcohols under mild conditions. The reaction tolerates many functional groups (such as carboxylic acids) that are incompatible with other methods. The alkyne addition reaction proceeds best using bulky phosphine ligands such as 2-(di-tert-butylphosphino)biphenyl. This method fills a void in the more common zinc-catalyzed processes, which give poor yields with enolizable 1,2-dicarbonyl substrates.

Authors+Show Affiliations

Department of Chemistry, 1-014 Center for Science and Technology, Syracuse University, New York 13244, USA.No affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

16381569

Citation

Dhondi, Pawan K., and John D. Chisholm. "Rhodium-catalyzed Addition of Alkynes to Activated Ketones and Aldehydes." Organic Letters, vol. 8, no. 1, 2006, pp. 67-9.
Dhondi PK, Chisholm JD. Rhodium-catalyzed addition of alkynes to activated ketones and aldehydes. Org Lett. 2006;8(1):67-9.
Dhondi, P. K., & Chisholm, J. D. (2006). Rhodium-catalyzed addition of alkynes to activated ketones and aldehydes. Organic Letters, 8(1), 67-9.
Dhondi PK, Chisholm JD. Rhodium-catalyzed Addition of Alkynes to Activated Ketones and Aldehydes. Org Lett. 2006 Jan 5;8(1):67-9. PubMed PMID: 16381569.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rhodium-catalyzed addition of alkynes to activated ketones and aldehydes. AU - Dhondi,Pawan K, AU - Chisholm,John D, PY - 2005/12/31/pubmed PY - 2005/12/31/medline PY - 2005/12/31/entrez SP - 67 EP - 9 JF - Organic letters JO - Org Lett VL - 8 IS - 1 N2 - [reaction: see text] The rhodium-catalyzed addition of alkynes to 1,2-diketones, 1,2-ketoesters, and aldehydes provides a method for the synthesis of tertiary alkynyl alcohols under mild conditions. The reaction tolerates many functional groups (such as carboxylic acids) that are incompatible with other methods. The alkyne addition reaction proceeds best using bulky phosphine ligands such as 2-(di-tert-butylphosphino)biphenyl. This method fills a void in the more common zinc-catalyzed processes, which give poor yields with enolizable 1,2-dicarbonyl substrates. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/16381569/Rhodium_catalyzed_addition_of_alkynes_to_activated_ketones_and_aldehydes_ L2 - https://doi.org/10.1021/ol0525260 DB - PRIME DP - Unbound Medicine ER -
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