Synthesis of 6‐Alkylated Phenanthridine Derivatives Using Photoredox Neutral Somophilic Isocyanide Insertion

Jiang, Heng; Cheng, Yuanzheng; Wang, Ru-Zhi; Zheng, Mengmeng; Zhang, Yan; Yu, Shouyun

doi:10.1002/ange.201308376

Cited by 54 publications

(9 citation statements)

References 94 publications

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“…Since 2-isocyanobiphenyls are effective radical acceptors 40 41 42 , we first selected them as the partners of N -protected amino acid active esters under the visible-light photoredox catalysis. As shown in Table 1 , our investigation for optimized conditions began by using model reaction of N -Boc-Pro-OPht (Pht = phthalimide) ( 1r ) with isonitrile 2a .…”

Section: Resultsmentioning

confidence: 99%

Installing amino acids and peptides on N-heterocycles under visible-light assistance

Jin

Jiang

Wang

et al. 2016

Sci Rep

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Readily available natural α-amino acids are one of nature’s most attractive and versatile building blocks in synthesis of natural products and biomolecules. Peptides and N-heterocycles exhibit various biological and pharmaceutical functions. Conjugation of amino acids or peptides with N-heterocycles provides boundless potentiality for screening and discovery of diverse biologically active molecules. However, it is a great challenge to install amino acids or peptides on N-heterocycles through formation of carbon-carbon bonds under mild conditions. In this article, eighteen N-protected α-amino acids and three peptides were well assembled on phenanthridine derivatives via couplings of N-protected α-amino acid and peptide active esters with substituted 2-isocyanobiphenyls at room temperature under visible-light assistance. Furthermore, N-Boc-proline residue was successfully conjugated with oxindole derivatives using similar procedures. The simple protocol, mild reaction conditions, fast reaction, and high efficiency of this method make it an important strategy for synthesis of diverse molecules containing amino acid and peptide fragments.

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Section: Resultsmentioning

confidence: 99%

Installing amino acids and peptides on N-heterocycles under visible-light assistance

Jin

Jiang

Wang

et al. 2016

Sci Rep

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“…Recently, our group became interested in visible light‐promoted somophilic triple bond insertions to provide functionalized (hetero)arenes 9. Comparing to biphenyl isocyanides, which have frequently been used to construct phenanthridine derivatives,9b,c,10 the chemistry of vinyl isocyanides remains mainly unexplored 11. Very recently, we reported the synthesis of 1‐arylisoquinoline derivatives using the somophilic insertion of vinyl isocyanides 9d.…”

Section: Optimization Of the Reaction Conditions[a]mentioning

confidence: 99%

Regiospecific Synthesis of 1‐Trifluoromethylisoquinolines Enabled by Photoredox Somophilic Vinyl Isocyanide Insertion

et al. 2014

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A strategy has been developed for the regiospecific synthesis of 1-trifluoromethylisoquinoline derivatives. This strategy is enabled by a photoredox vinyl isocyanide insertion with the help of Umemotos reagent. The methodology presented here provides an access to highly fuctionalized 1-trifluoromethylisoquinolines regiospecifically under mild conditions in good-to-excellent chemical yields. A detailed mechanism is proposed, which is supported by experiments and theoretical calculations.

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“…According to previous reports, 1,17 a plausible mechanism was proposed (Scheme 1). The photocatalyst was excited to Creating useful and functional substance is one of the most important objectives of synthesis.…”

Section: The Journal Of Organic Chemistrymentioning

confidence: 85%

Visible Light-Induced Radical Cyclization of Tertiary Bromides with Isonitriles To Construct Trifluoromethylated Quaternary Carbon Center

et al. 2018

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The reaction of trifluoromethylated tertiary bromides with isonitriles induced by visible light is reported. Defluorination was avoided in a radical process. This method provides an efficient approach to compounds containing a trifluoromethylated quaternary carbon center, most of which show excellent potential to be agrochemicals. In addition, the bromides were prepared from perfluoroisobutylene, which is a waste from industry, after several steps. This reaction shows a feasible transfer of harmful waste into useful compounds.

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Synthesis of 6‐Alkylated Phenanthridine Derivatives Using Photoredox Neutral Somophilic Isocyanide Insertion

Cited by 54 publications

References 94 publications

Installing amino acids and peptides on N-heterocycles under visible-light assistance

Installing amino acids and peptides on N-heterocycles under visible-light assistance

Regiospecific Synthesis of 1‐Trifluoromethylisoquinolines Enabled by Photoredox Somophilic Vinyl Isocyanide Insertion

Visible Light-Induced Radical Cyclization of Tertiary Bromides with Isonitriles To Construct Trifluoromethylated Quaternary Carbon Center

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