One-Carbon Oxidative Annulations of 1,3-Enynes by Catalytic C-H Functionalization and 1,4-Rhodium(III) Migration.
Chemistry. 2018 Mar 15; 24(16):4050-4054.C

Abstract

Rhodium(III)-catalyzed C-H functionalization-oxidative annulations of aromatic substrates with 1,3-enynes that contain allylic hydrogen atoms cis to the alkyne are described. The key step in these reactions is an alkenyl-to-allyl 1,4-rhodium(III) migration to give electrophilic π-allylrhodium(III) species. Nucleophilic trapping of these species gives heterocycles such as benzopyrans, isobenzofuranones, and isoindolinones.

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Authors+Show Affiliations

Dooley JD

EaStCHEM, School of Chemistry, University of Edinburgh, Joseph Black Building, The King's Buildings, David Brewster Road, Edinburgh, EH9 3FJ, UK.

Lam HW

The GSK Carbon Neutral Laboratories for Sustainable Chemistry, University of Nottingham, Jubilee Campus, Triumph Road Nottingham, NG7 2TU (UK) and School of Chemistry, University of Nottingham, University Park Nottingham, NG7 2RD, UK.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

29356188

Citation

Dooley, Johnathon D., and Hon Wai Lam. "One-Carbon Oxidative Annulations of 1,3-Enynes By Catalytic C-H Functionalization and 1,4-Rhodium(III) Migration." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 24, no. 16, 2018, pp. 4050-4054.

Dooley JD, Lam HW. One-Carbon Oxidative Annulations of 1,3-Enynes by Catalytic C-H Functionalization and 1,4-Rhodium(III) Migration. Chemistry. 2018;24(16):4050-4054.

Dooley, J. D., & Lam, H. W. (2018). One-Carbon Oxidative Annulations of 1,3-Enynes by Catalytic C-H Functionalization and 1,4-Rhodium(III) Migration. Chemistry (Weinheim an Der Bergstrasse, Germany), 24(16), 4050-4054. https://doi.org/10.1002/chem.201706043

Dooley JD, Lam HW. One-Carbon Oxidative Annulations of 1,3-Enynes By Catalytic C-H Functionalization and 1,4-Rhodium(III) Migration. Chemistry. 2018 Mar 15;24(16):4050-4054. PubMed PMID: 29356188.

* Article titles in AMA citation format should be in sentence-case

TY - JOUR T1 - One-Carbon Oxidative Annulations of 1,3-Enynes by Catalytic C-H Functionalization and 1,4-Rhodium(III) Migration. AU - Dooley,Johnathon D, AU - Lam,Hon Wai, Y1 - 2018/02/21/ PY - 2017/12/20/received PY - 2018/1/23/pubmed PY - 2018/1/23/medline PY - 2018/1/23/entrez KW - C−H functionalization KW - catalysis KW - enyne KW - isomerization KW - rhodium SP - 4050 EP - 4054 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 24 IS - 16 N2 - Rhodium(III)-catalyzed C-H functionalization-oxidative annulations of aromatic substrates with 1,3-enynes that contain allylic hydrogen atoms cis to the alkyne are described. The key step in these reactions is an alkenyl-to-allyl 1,4-rhodium(III) migration to give electrophilic π-allylrhodium(III) species. Nucleophilic trapping of these species gives heterocycles such as benzopyrans, isobenzofuranones, and isoindolinones. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/29356188/One_Carbon_Oxidative_Annulations_of_13_Enynes_by_Catalytic_C_H_Functionalization_and_14_Rhodium_III__Migration_ DB - PRIME DP - Unbound Medicine ER -

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One-Carbon Oxidative Annulations of 1,3-Enynes by Catalytic C-H Functionalization and 1,4-Rhodium(III) Migration.Chemistry. 2018 Mar 15; 24(16):4050-4054.C