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.
Links
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 -