Ru(ii)-catalysed oxidative (4+2) annulation of chromene and coumarin carboxylic acids with alkynes/propargylic alcohols: isolation of Ru(0) complexes

Ru(ii)-catalysed oxidative (4 + 2) annulation of chromene and coumarin-3-carboxylic acids with alkynes/propargylic alcohols via sp(2) C-H bond activation is reported. While the reaction with alkynes affords highly substituted pyrano-chromones in good to excellent yields, the use of methyl-tethered p...

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Bibliographic Details
Published in:Organic & biomolecular chemistry Vol. 21; no. 1; pp. 195 - 208
Main Authors: Shankar, Mallepalli, Swamy, K. C. Kumara
Format: Journal Article
Language:English
Published: CAMBRIDGE Royal Soc Chemistry 21.12.2022
Subjects:
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
H BOND ACTIVATION
FUNCTIONALIZATION
ACRYLIC-ACIDS
AROMATIC-ACIDS
ALPHA-PYRONES
ISOCOUMARINS
ALKYNES
DERIVATIVES
CYCLIZATION
BENZOIC-ACIDS
ISSN:1477-0520, 1477-0539, 1477-0539
Online Access:Get more information
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Summary:Ru(ii)-catalysed oxidative (4 + 2) annulation of chromene and coumarin-3-carboxylic acids with alkynes/propargylic alcohols via sp(2) C-H bond activation is reported. While the reaction with alkynes affords highly substituted pyrano-chromones in good to excellent yields, the use of methyl-tethered propargylic alcohols in place of alkynes leads to novel Ru(0)-metal complexes in moderate to good yields; these complexes were stable in MeCO2H/O-2. The generality of the reaction with alkynes is illustrated in the case of both symmetrical and unsymmetrical internal alkynes with excellent regioselectivity in the case of unsymmetrical alkynes.
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ISSN:1477-0520
1477-0539
1477-0539
DOI:10.1039/d2ob01890j