Continuous Flow-Enabled Synthesis of Bench-Stable Bicyclo[1.1.1]pentane Trifluoroborate Salts and Their Utilization in Metallaphotoredox Cross-Couplings

Bicyclo­[1.1.1]­pentane motifs have gained increasing popularity in medicinal chemistry as bioisosteres because of their ability to impact key physicochemical properties. However, reports of direct C­(sp2)–C­(sp3) cross-coupling of these fragments to afford biaryl isosteres have been scarce. Herein...

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Bibliographic Details
Published inOrganic letters Vol. 22; no. 4; pp. 1648 - 1654
Main Authors VanHeyst, Michael D, Qi, Ji, Roecker, Anthony J, Hughes, Jonathan M. E, Cheng, Lili, Zhao, Zheyu, Yin, Jingjun
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.02.2020
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
2-TRIFLUOROBORATOCHROMANONES
DESIGN
MERGING PHOTOREDOX
NICKEL CATALYSIS
DECARBOXYLATIVE ARYLATION
ESTERS
BIOLOGICAL EVALUATION
ALPHA-AMINO-ACIDS
GENERATION
BROMIDES
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Summary:Bicyclo­[1.1.1]­pentane motifs have gained increasing popularity in medicinal chemistry as bioisosteres because of their ability to impact key physicochemical properties. However, reports of direct C­(sp2)–C­(sp3) cross-coupling of these fragments to afford biaryl isosteres have been scarce. Herein we describe the development of continuous flow-enabled synthesis of bench-stable bicyclo[1.1.1]­pentane trifluoroborate salts. Furthermore, we demonstrate the use of metallaphotoredox conditions to enable cross-coupling of these building blocks with complex aryl halide substrates.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c00242