A tunable synthesis of indigoids: targeting indirubin through temperature

The spontaneous conversion of 3-indoxyl to indigo is a well-established process used to produce indigo dyes. It was recently shown that some indoles, when reacted with molybdenum hexacarbonyl and cumyl peroxide, proceed through an indoxyl intermediate to produce significant amounts of indirubin thro...

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Bibliographic Details
Published in:RSC advances 2022-02, Vol.12 (9), p.547-5414
Main Authors: Shriver, James A, Kaller, Kaylie S, Kinsey, Ally L, Wang, Katelyn R, Sterrenberg, Summer R, Van Vors, Madison K, Cheek, Joshua T, Horner, John S
Format: Article
Language:English
Subjects:
Aldehydes
Carbonyls
Carboxylic acids
Chemistry
Functional groups
Indigo
Indoles
Substitutes
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Summary:The spontaneous conversion of 3-indoxyl to indigo is a well-established process used to produce indigo dyes. It was recently shown that some indoles, when reacted with molybdenum hexacarbonyl and cumyl peroxide, proceed through an indoxyl intermediate to produce significant amounts of indirubin through a competing mechanism. Modulation of this system to lower temperatures allows for careful tuning, leading to selective production of indirubins in a general process. A systematic assay of indoles show that electron deficient indoles work well when substituted at the 5 and 7 positions. In contrast, 6-substituted electron rich indoles give the best results whereas halogeno indoles work well in all cases. This process shows broad functional group tolerance for generally reactive carbonyl-containing compounds such as aldehydes and carboxylic acids. Selectivity of indigoid synthesis shifts from indigo to indirubin at reduced temperatures across a range of substrates.
ISSN:2046-2069
2046-2069
DOI:10.1039/d2ra00400c