Palladium-catalyzed α-arylation of indolin-3-ones

A method for the catalytic α-arylation of indolin-3-ones was developed. The catalytic system comprising Pd(dba) 2 and PAd 3 was found to be optimal for the transformation. The protocol features broad functional group compatibility in that a range of arylated indoxyl derivatives bearing a fully subst...

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Published inChemical communications (Cambridge, England) Vol. 56; no. 34; pp. 466 - 4663
Main Authors Chang, Yu-Hsuan, Peng, Wan-Ling, Chen, I-Chia, Hsu, Hsin-Yun, Wu, Yen-Ku
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 30.04.2020
Royal Society of Chemistry
Subjects
antineoplastic activity
arylation
bioassays
carbon
catalytic activity
cell lines
Chemistry
Chemistry, Multidisciplinary
cytotoxicity
Functional groups
neoplasm cells
neoplasms
Palladium
Physical Sciences
Science & Technology
Substitutes
OXINDOLES
Online AccessGet full text
ISSN1359-7345
1364-548X
1364-548X
DOI10.1039/d0cc00435a

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Abstract A method for the catalytic α-arylation of indolin-3-ones was developed. The catalytic system comprising Pd(dba) 2 and PAd 3 was found to be optimal for the transformation. The protocol features broad functional group compatibility in that a range of arylated indoxyl derivatives bearing a fully substituted carbon center was synthesized with high efficiency. A preliminary bioassay study revealed that the selected indole-substituted indolin-3-ones exhibit favorable cytotoxic activities against HCT-116 cancer cell line. A general route to C2-(hetero)arylated indolin-3-ones bearing a fully substituted α-center was established.
AbstractList A method for the catalytic α-arylation of indolin-3-ones was developed. The catalytic system comprising Pd(dba)₂ and PAd₃ was found to be optimal for the transformation. The protocol features broad functional group compatibility in that a range of arylated indoxyl derivatives bearing a fully substituted carbon center was synthesized with high efficiency. A preliminary bioassay study revealed that the selected indole-substituted indolin-3-ones exhibit favorable cytotoxic activities against HCT-116 cancer cell line.
A method for the catalytic α-arylation of indolin-3-ones was developed. The catalytic system comprising Pd(dba)2 and PAd3 was found to be optimal for the transformation. The protocol features broad functional group compatibility in that a range of arylated indoxyl derivatives bearing a fully substituted carbon center was synthesized with high efficiency. A preliminary bioassay study revealed that the selected indole-substituted indolin-3-ones exhibit favorable cytotoxic activities against HCT-116 cancer cell line.
A method for the catalytic α-arylation of indolin-3-ones was developed. The catalytic system comprising Pd(dba) 2 and PAd 3 was found to be optimal for the transformation. The protocol features broad functional group compatibility in that a range of arylated indoxyl derivatives bearing a fully substituted carbon center was synthesized with high efficiency. A preliminary bioassay study revealed that the selected indole-substituted indolin-3-ones exhibit favorable cytotoxic activities against HCT-116 cancer cell line.
A method for the catalytic α-arylation of indolin-3-ones was developed. The catalytic system comprising Pd(dba) and PAd was found to be optimal for the transformation. The protocol features broad functional group compatibility in that a range of arylated indoxyl derivatives bearing a fully substituted carbon center was synthesized with high efficiency. A preliminary bioassay study revealed that the selected indole-substituted indolin-3-ones exhibit favorable cytotoxic activities against HCT-116 cancer cell line.
A method for the catalytic α-arylation of indolin-3-ones was developed. The catalytic system comprising Pd(dba)2 and PAd3 was found to be optimal for the transformation. The protocol features broad functional group compatibility in that a range of arylated indoxyl derivatives bearing a fully substituted carbon center was synthesized with high efficiency. A preliminary bioassay study revealed that the selected indole-substituted indolin-3-ones exhibit favorable cytotoxic activities against HCT-116 cancer cell line.A method for the catalytic α-arylation of indolin-3-ones was developed. The catalytic system comprising Pd(dba)2 and PAd3 was found to be optimal for the transformation. The protocol features broad functional group compatibility in that a range of arylated indoxyl derivatives bearing a fully substituted carbon center was synthesized with high efficiency. A preliminary bioassay study revealed that the selected indole-substituted indolin-3-ones exhibit favorable cytotoxic activities against HCT-116 cancer cell line.
A method for the catalytic alpha-arylation of indolin-3-ones was developed. The catalytic system comprising Pd(dba)(2) and PAd(3) was found to be optimal for the transformation. The protocol features broad functional group compatibility in that a range of arylated indoxyl derivatives bearing a fully substituted carbon center was synthesized with high efficiency. A preliminary bioassay study revealed that the selected indole-substituted indolin-3-ones exhibit favorable cytotoxic activities against HCT-116 cancer cell line.
A method for the catalytic α-arylation of indolin-3-ones was developed. The catalytic system comprising Pd(dba) 2 and PAd 3 was found to be optimal for the transformation. The protocol features broad functional group compatibility in that a range of arylated indoxyl derivatives bearing a fully substituted carbon center was synthesized with high efficiency. A preliminary bioassay study revealed that the selected indole-substituted indolin-3-ones exhibit favorable cytotoxic activities against HCT-116 cancer cell line. A general route to C2-(hetero)arylated indolin-3-ones bearing a fully substituted α-center was established.
Author Chen, I-Chia
Chang, Yu-Hsuan
Peng, Wan-Ling
Hsu, Hsin-Yun
Wu, Yen-Ku
AuthorAffiliation Department of Cosmetic Applications and Management, Cardinal Tien Junior College of Healthcare and Management
Department of Applied Chemistry
National Chiao Tung University
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SSID ssj0000158
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Snippet A method for the catalytic α-arylation of indolin-3-ones was developed. The catalytic system comprising Pd(dba) 2 and PAd 3 was found to be optimal for the...
A method for the catalytic alpha-arylation of indolin-3-ones was developed. The catalytic system comprising Pd(dba)(2) and PAd(3) was found to be optimal for...
A method for the catalytic α-arylation of indolin-3-ones was developed. The catalytic system comprising Pd(dba) and PAd was found to be optimal for the...
A method for the catalytic α-arylation of indolin-3-ones was developed. The catalytic system comprising Pd(dba)2 and PAd3 was found to be optimal for the...
A method for the catalytic α-arylation of indolin-3-ones was developed. The catalytic system comprising Pd(dba)₂ and PAd₃ was found to be optimal for the...
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SubjectTerms antineoplastic activity
arylation
bioassays
carbon
catalytic activity
cell lines
Chemistry
Chemistry, Multidisciplinary
cytotoxicity
Functional groups
neoplasm cells
neoplasms
Palladium
Physical Sciences
Science & Technology
Substitutes
Title Palladium-catalyzed α-arylation of indolin-3-ones
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