The transient-chelating-group-controlled stereoselective Rh()-catalyzed silylative aminocarbonylation of 2-alkynylanilines: access to ()-3-(silylmethylene)indolin-2-ones

A new method involving mild acryl transient-chelating-group-controlled stereoselective Rh( i )-catalyzed silylative aminocarbonylation of 2-alkynylanilines with CO and silanes is presented for producing ( Z )-3-(silylmethylene)indolin-2-ones. Upon using an acryl transient chelating group, 2-alkynyla...

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Published inChemical science (Cambridge) Vol. 13; no. 32; pp. 9425 - 9431
Main Authors Han, Ya-Fei, Lv, Gui-Fen, Li, Yang, Wu, Li-Jun, Ouyang, Xuan-Hui, Li, Jin-Heng
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 17.08.2022
Royal Society of Chemistry
The Royal Society of Chemistry
Subjects
Alkynes
Chelation
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
Stereoselectivity
3-ALKYLIDENEOXINDOLES
OXINDOLE SYNTHESIS
NATURAL-PRODUCTS
CATALYZED CYCLIZATION REACTION
SELECTIVE SYNTHESIS
BOND ACTIVATION
C-H FUNCTIONALIZATION
2-(ALKYNYL)ARYL ISOCYANATES
CLEAVAGE
DERIVATIVES
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Summary:A new method involving mild acryl transient-chelating-group-controlled stereoselective Rh( i )-catalyzed silylative aminocarbonylation of 2-alkynylanilines with CO and silanes is presented for producing ( Z )-3-(silylmethylene)indolin-2-ones. Upon using an acryl transient chelating group, 2-alkynylanilines undergo an unprecedented alkyne cis -silylrhodation followed by aminocarbonylation to assemble ( Z )-3-(silylmethylene)indolin-2-ones. Mechanistic studies show that acryl transient chelating effects result in the key alkyne cis -silylrhodation process. Transient-chelating-group-controlled stereoselective rhodium(I)-catalyzed silylative aminocarbonylation of 2- alkynylanilines with CO and silanes toward (Z)-3-(silylmethylene)indolin-2-ones is presented.
Bibliography:https://doi.org/10.1039/d2sc03009h
Electronic supplementary information (ESI) available. See
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ISSN:2041-6520
2041-6539
DOI:10.1039/d2sc03009h