Cooperative Noncovalent Interactions Lead to a Highly Diastereoselective Sulfonyl-Directed Fluorination of Steroidal α,β-Unsaturated Hydrazones

Capilato, Joseph N.; Siegler, Maxime A.; Rowshanpour, Rozhin; Dudding, Travis; Lectka, Thomas

doi:10.1021/acs.joc.0c02716

Cited by 4 publications

(1 citation statement)

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“…Modern-day organic synthesis hinges upon efficiency and well-understood mechanisms for securing important chemical targets, such as organofluorine compounds. In this chemical space, growing interest in fluorinated compounds and strategies for their streamlined synthesis is of utmost importance. , In highlighting this status, is an impressive global market of fluorinated compounds, estimated at approximately 20 billion (USD) in the year 2022 and extensive applications in drug development, pharmaceutical synthesis, chemical biology, ion sensing, self-assembly, fluorescence, materials chemistry, and mechanochemistry. − …”

Section: Introductionmentioning

confidence: 99%

Streamlining Fluoroalkenyl Arene Synthesis Illuminated with Mechanistic Insights

Rajabalinia,

Hoford,

Dudding

2024

ACS Omega

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Fluorinated compounds are a staple of modern-day chemical innovation, and efficient strategies for their synthesis are highly valuable. In this chemical space, fluoroalkenes continue to be the object of much interest across diverse fields, including drug development and pharmaceuticals with active roles as bioisosteres. Herein, in expanding chemists' synthetic toolbox for constructing valuable organofluorine compounds, we report a "pipeline" strategy for the synthesis of fluorinated olefins, viz., gem-difluoroalkenyl and monofluoroalkenyl arenes with high E-isomeric selectivity. The advantages of this streamlined synthetic protocol include mild reaction conditions, operational simplicity, broad substrate scope, and good to excellent yields, even at gram scales. Critical to this robust procedure is the use of widely available and inexpensive "scavenger" solid-support Merrifield peptide resin for removing phosphine impurities. Further computational investigations offering clarity into this reactivity are disclosed.

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