A Convenient Palladium‐Catalyzed Carbonylative Synthesis of (E)‐3‐Benzylidenechroman‐4‐ones

A convenient palladium‐catalyzed carbonylation reaction for the efficient synthesis of (E)‐3‐benzylidenechroman‐4‐ones has been developed. Using TFBen as a solid CO source, a range of substituted (E)‐3‐benzylidenechroman‐4‐ones were prepared in moderate to good yields with 2‐iodophenols and allyl ch...

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Bibliographic Details
Published in:Chemistry : a European journal 2019-03, Vol.25 (14), p.3521-3524
Main Authors: Wang, Wei‐Feng, Peng, Jin‐Bao, Qi, Xinxin, Ying, Jun, Wu, Xiao‐Feng
Format: Article
Language:English
Subjects:
Allyl chloride
benzylidenechromanone
carbonylation
Carbonyls
cascade reaction
Chemical synthesis
Chemistry
heterocycle synthesis
Palladium
palladium catalyst
Substitutes
Substrates
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Summary:A convenient palladium‐catalyzed carbonylation reaction for the efficient synthesis of (E)‐3‐benzylidenechroman‐4‐ones has been developed. Using TFBen as a solid CO source, a range of substituted (E)‐3‐benzylidenechroman‐4‐ones were prepared in moderate to good yields with 2‐iodophenols and allyl chlorides as the substrates. Additionally, substituted quinolin‐4(1H)‐ones can also be obtained with 2‐iodoaniline as the starting material. Cascade reactions: A palladium‐catalyzed carbonylation reaction for the synthesis of benzylidenechromanone has been developed. Using 2‐iodophenols and allyl chlorides as the substrates, a range of substituted benzylidenechromanones were prepared in moderate to good yields. Additionally, substituted quinolin‐4(1H)‐one derivatives could also be obtained when 2‐iodoanilines were used (see scheme).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201900015