High-Throughput Approach toward the Development of a Mizoroki–Heck Reaction To Access Tricyclic Spirolactones

Annand, James R.; Riehl, Paul S.; Schultz, Danielle M.; Schindler, Corinna S.

doi:10.1021/acs.joc.0c00997

Cited by 3 publications

(1 citation statement)

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“…A Mizoroki‐Heck approach was similarly used to demonstrate the synthesis of a tricyclic spirolactone by evaluating 24 unique HTE conditions using four ligands and six base combinations to identify optimized conditions for synthesizing the target in high regioselectivity and high yield [25] . (Scheme 2a).…”

Section: C−c Bond Forming Reactionsmentioning

confidence: 99%

Advancement in Organic Synthesis Through High Throughput Experimentation

2021

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and cyanoarenes has also been optimized using an HTE approach. [63] Other Photochemical TransformationsNon-activated alkyl bromides were coupled with Michael acceptors in a photoredox Giese-type reaction. [64] Reaction optimization was performed by studying the effect of photocatalyst, solvent, base, and varying amounts of radical initiator (Me 3 Si) 3 SiH on product and by-product profile. Another study of conjugate addition using photocatalytic methodology was shown for the synthesis of unnatural β-alkyl α-amino acid derivatives via decarboxylative photocatalysis. [65] Photocatalysis was performed with oxime and cyanopyridine precursors (Scheme 4g) to form primary amine products. [66] Four different solvents (acetone, DCE, ACN, DMSO), nine different photocatalysts, and two reductants were used to evaluate 45 unique reactions. DMSO with diisopropylamine and Ir[dF(Me) ppy] 2 dtbbpyPF 6 gave the highest yield by UPLC, although many Scheme 4. Photocatalytic transformations in HTE.

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Section: C−c Bond Forming Reactionsmentioning

confidence: 99%