Recent quinone diazide based transformations via metal–carbene formation

Recent quinone diazide based transformations via metal–carbene formation

The diazo quinone or quinone diazide class of compounds has been extensively utilised to introduce phenol/naphthol moieties into hydrocarbons or nitrogen-containing heterocycles under transition metal catalysis. The reactions proceed via C–H insertion or migratory insertion of metal carbenes. In man...

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Veröffentlicht in:New journal of chemistry 2021-06, Vol.45 (23), p.10135-10149
Hauptverfasser: Bera, Satabdi, Sarkar, Souradip, Samanta, Rajarshi
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Sprache:eng
Schlagworte:
Carbenes
Chirality
Enantiomers
Insertion
Naphthol
Phenols
Quinones
Transition metals
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Sarkar, Souradip
Samanta, Rajarshi
description The diazo quinone or quinone diazide class of compounds has been extensively utilised to introduce phenol/naphthol moieties into hydrocarbons or nitrogen-containing heterocycles under transition metal catalysis. The reactions proceed via C–H insertion or migratory insertion of metal carbenes. In many cases, the site-selectivities were obtained via the guidance of directing groups. Various rearrangement reactions were explored with the metal carbenes generated from these diazo compounds. Further, interesting asymmetric reactions were studied to obtain phenol/naphthol containing compounds having stereogenic centers or axial chirality with high enantioselectivity. In this review, the recent progress on synthetic studies of metal carbenes generated from quinone diazide moieties has been summarized.
doi_str_mv 10.1039/D1NJ01678D
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source Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects Carbenes
Chirality
Enantiomers
Insertion
Naphthol
Phenols
Quinones
Transition metals
title Recent quinone diazide based transformations via metal–carbene formation
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