Catalytic 1,4-rhodium(III) migration enables 1,3-enynes to function as one-carbon oxidative annulation partners in C-H functionalizations.Angew Chem Int Ed Engl. 2014 Sep 08; 53(37):9931-5.AC
Abstract
1,3-Enynes containing allylic hydrogens cis to the alkyne are shown to act as one-carbon partners, rather than two-carbon partners, in various rhodium-catalyzed oxidative annulations. The mechanism of these unexpected transformations is proposed to occur through double C-H activation, involving a hitherto rare example of the 1,4-migration of a Rh(III) species. This phenomenon is general across a variety of substrates, and provides a diverse range of heterocyclic products.
Links
Pub Type(s)
Journal Article
Language
eng
PubMed ID
25048465
Citation
Burns, David J., and Hon Wai Lam. "Catalytic 1,4-rhodium(III) Migration Enables 1,3-enynes to Function as One-carbon Oxidative Annulation Partners in C-H Functionalizations." Angewandte Chemie (International Ed. in English), vol. 53, no. 37, 2014, pp. 9931-5.
Burns DJ, Lam HW. Catalytic 1,4-rhodium(III) migration enables 1,3-enynes to function as one-carbon oxidative annulation partners in C-H functionalizations. Angew Chem Int Ed Engl. 2014;53(37):9931-5.
Burns, D. J., & Lam, H. W. (2014). Catalytic 1,4-rhodium(III) migration enables 1,3-enynes to function as one-carbon oxidative annulation partners in C-H functionalizations. Angewandte Chemie (International Ed. in English), 53(37), 9931-5. https://doi.org/10.1002/anie.201406072
Burns DJ, Lam HW. Catalytic 1,4-rhodium(III) Migration Enables 1,3-enynes to Function as One-carbon Oxidative Annulation Partners in C-H Functionalizations. Angew Chem Int Ed Engl. 2014 Sep 8;53(37):9931-5. PubMed PMID: 25048465.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR
T1 - Catalytic 1,4-rhodium(III) migration enables 1,3-enynes to function as one-carbon oxidative annulation partners in C-H functionalizations.
AU - Burns,David J,
AU - Lam,Hon Wai,
Y1 - 2014/07/22/
PY - 2014/06/10/received
PY - 2014/7/23/entrez
PY - 2014/7/23/pubmed
PY - 2014/7/23/medline
KW - CH functionalization
KW - catalysis
KW - enyne
KW - oxidation
KW - rhodium
SP - 9931
EP - 5
JF - Angewandte Chemie (International ed. in English)
JO - Angew Chem Int Ed Engl
VL - 53
IS - 37
N2 - 1,3-Enynes containing allylic hydrogens cis to the alkyne are shown to act as one-carbon partners, rather than two-carbon partners, in various rhodium-catalyzed oxidative annulations. The mechanism of these unexpected transformations is proposed to occur through double C-H activation, involving a hitherto rare example of the 1,4-migration of a Rh(III) species. This phenomenon is general across a variety of substrates, and provides a diverse range of heterocyclic products.
SN - 1521-3773
UR - https://www.unboundmedicine.com/medline/citation/25048465/Catalytic_14_rhodium_III__migration_enables_13_enynes_to_function_as_one_carbon_oxidative_annulation_partners_in_C_H_functionalizations_
DB - PRIME
DP - Unbound Medicine
ER -
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