Divergent synthesis of difluoromethylated indole-3-carbinols, bisindolylmethanes and indole-3-methanamines
Literature Information
Yifei Qu, Xiaojia Cai, Yuzhuang Guan, Jiamin Tan, Zhangping Cai, Minyun Liu, Yasi Huang, Jinhui Hu, Wen-Hua Chen, Jia-Qiang Wu
Indole-3-carbinol, bisindolylmethanes (BIMs) and indole-3-methanamines exhibit diverse therapeutic activities. Fluorinated molecules are widely used in pharmaceuticals. Herein we report a facile and straightforward method for the successful synthesis of difluoromethylated indole-3-carbinols, bisindolylmethanes and indole-3-methanamines by a Friedel–Crafts reaction. The reaction involves the in situ generation of difluoroacetaldehyde from difluoroacetaldehyde ethyl hemiacetal in the presence of a base or an acid. This protocol is distinguished by its good to excellent yields, broad substrate compatibility, good functional group tolerance and scalability.
Related Literature
Nitrile stabilized synthesis of pyrrolidine and piperidine derivatives via tandem alkynyl aza-Prins–Ritter reactions
Sudip Shit, Chinmayee Choudhury, Anil K. Saikia
DOI: 10.1039/D3OB01764H
Sequential Dieckmann cyclization enables the total synthesis of 7-epi-clusianone and 18-hydroxy-7-epi-clusianone
Yunhui Wan, Huaimo Wu, Linhao Xia, Song Liu, Yi Ren, Hongxi Xu, Changwu Zheng
DOI: 10.1039/D3OB01840G
Catalyst-free photo-induced aerobic radical synthesis of lactams from N-alkenyl trichloroacetamides in 2-methyltetrahydrofuran as the radical initiator under violet light
Faïza Diaba, Gisela Trenchs
DOI: 10.1039/D3OB01804K
Photo-induced radical transformations of tosyl cyanide
Ya Liu, Rui Li, Bing Yu
DOI: 10.1039/D3OB01771K
A chloride-responsive molecular switch: driving ion transport and empowering antibacterial properties
Sribash Das, Rama Karn, Mohit Kumar, Soumya Srimayee
DOI: 10.1039/D3OB01826A
α-Alkylation of ketones with primary alcohols by an active non-noble metal Cu/CuOx catalyst
Hongli Wang, Chun-Ran Chang
DOI: 10.1039/D3OB01836A
Synthesis of Cs-symmetrical C60 tetra-adducts via reactions of C60Cl6 with CH-acids and enol silyl ester
Olga A. Kraevaya, Alexander S. Peregudov
DOI: 10.1039/D3OB01868G
You might also like
What regulatory guidelines apply to 4-Amino-3-bromophenol (CAS: 74440-80-5)?
4-Amino-3-bromophenol (CAS: 74440-80-5) falls under the classification of a haza...
How should (17beta)-3-Oxoestr-4-en-17-yl acetate (CAS: 1425-10-1) be stored?
(17beta)-3-Oxoestr-4-en-17-yl acetate should be stored in a cool, dry place away...
What are the physical and chemical properties of 2-[(2,2-Diethoxyethyl)disulfanyl]-1,1-diethoxyethane (CAS: 76505-71-0)?
2-[(2,2-Diethoxyethyl)disulfanyl]-1,1-diethoxyethane (CAS: 76505-71-0) is a colo...
What is the market or research trend for 1-(β-D-ribofuranosyl)-1H-imidazo[4,5-c]pyridin-4-amine?
The market and research for 1-(β-D-ribofuranosyl)-1H-imidazo[4,5-c]pyridin-4-ami...
How should waste containing Conjugated Estrogen (CAS: 12126-59-9) be handled?
Waste containing Conjugated Estrogen (CAS: 12126-59-9) should be collected and d...
What is the market or research trend for Bis(2,2,2-trifluoroethyl) (methoxycarbonylmethyl)phosphonate?
The market for Bis(2,2,2-trifluoroethyl) (methoxycarbonylmethyl)phosphonate (CAS...
Are there alternatives to 3,4'-Di-O-methylellagic acid (CAS: 57499-59-9) in synthesis?
There are several alternatives to 3,4'-Di-O-methylellagic acid (CAS: 57499-59-9)...
What regulatory guidelines apply to 2-Chloro-N,N-dimethylpyridin-4-amine (CAS: 59047-70-0)?
2-Chloro-N,N-dimethylpyridin-4-amine (CAS: 59047-70-0) is regulated under the Gl...
What is cerium(3+);oxygen(2-);vanadium(5+) (CAS: 13597-19-8)?
Cerium(3+);oxygen(2-);vanadium(5+) (CAS: 13597-19-8) is a complex inorganic comp...
Is 7-Chloro-1-iodoisoquinoline (CAS: 1203579-27-4) safe?
7-Chloro-1-iodoisoquinoline (CAS: 1203579-27-4) is generally considered safe whe...
Source Journal
Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.










![5,10-Dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one structure 5,10-Dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one structure](https://static.chemtradehub.com/structs/581/5814-41-5-0b01.webp)



![4-{2-[(9H-Fluoren-9-ylmethoxy)carbonyl]hydrazino}benzoic acid structure 4-{2-[(9H-Fluoren-9-ylmethoxy)carbonyl]hydrazino}benzoic acid structure](https://static.chemtradehub.com/structs/214/214475-53-3-bf36.webp)