Synthesis of Cycloalkyl Substituted 7‑Azaindoles via Photoredox Nickel Dual Catalytic Cross-Coupling in Batch and Continuous Flow

An efficient photoredox/Ni dual catalytic Csp2 –Csp3 cross-coupling protocol in a continuous-flow regime to synthesize a variety of regioisomeric cycloalkyl substituted 7-azaindoles has been developed. These transformations proceed efficiently under mild conditions (blue LED light irradiation at 30...

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Bibliographic Details
Published inOrganic letters Vol. 18; no. 23; pp. 6180 - 6183
Main Authors Palaychuk, Natalie, DeLano, Travis J, Boyd, Michael J, Green, Jeremy, Bandarage, Upul K
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.12.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
PHOTOCHEMISTRY
POTENT
INHIBITORS
TECHNOLOGY
DISCOVERY
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Summary:An efficient photoredox/Ni dual catalytic Csp2 –Csp3 cross-coupling protocol in a continuous-flow regime to synthesize a variety of regioisomeric cycloalkyl substituted 7-azaindoles has been developed. These transformations proceed efficiently under mild conditions (blue LED light irradiation at 30 °C over 40 min residence time in mixed solvent systems). Reactions are easy to perform and afford most of the desired 2-, 3-, 4-, 5-, and 6-cycloalkyl substituted 7-azaindoles in moderate-to-good yield.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b03223