Rhodium-Catalyzed Carbonylative Synthesis of Aryl Salicylates from Unactivated Phenols

A rhodium-catalyzed carbonylative transformation of unactivated phenols to aryl salicylates is described. This protocol is characterized by utilizing 1,3-rhodium migration as the key step to provide direct access to synthesize o-hydroxyaryl esters. Various desired aryl o-hydroxybenzoates were produc...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 22; no. 15; pp. 6050 - 6054
Main Authors Ai, Han-Jun, Zhang, Youcan, Zhao, Fengqian, Wu, Xiao-Feng
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.08.2020
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
OXIDATIVE CARBONYLATION
MIGRATION
PHOSGENE
DIMETHYL CARBONATE
FRIES REARRANGEMENT
SMILES REARRANGEMENT
DIPHENYL CARBONATE
C-C
INTERNAL ALKYNES
CLEAVAGE
Online AccessGet full text

Cover

More Information
Summary:A rhodium-catalyzed carbonylative transformation of unactivated phenols to aryl salicylates is described. This protocol is characterized by utilizing 1,3-rhodium migration as the key step to provide direct access to synthesize o-hydroxyaryl esters. Various desired aryl o-hydroxybenzoates were produced in moderate to excellent yields with bis­(dicyclohexylphosphino)­ethane (DCPE) as the ligand. Interestingly, diphenyl carbonate was formed as the main product when 1,3-bis­(diphenylphosphino)­propane (DPPP) was used as the ligand. A plausible reaction mechanism is proposed.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c02133