Chemoselective Dehydrogenation and Hetero-Arylation of Amides via Radical Translocation Enabled by Photoexcited Triplet Ketone Catalysis DOI

Akash Bisoyi,

Amit Behera,

Alisha Rani Tripathy

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 16, 2024

We herein report the chemoselective dehydrogenation and heteroarylation of amides through photoexcited triplet ketone catalysis. Under mild reaction conditions, generated aryl radical halogen atom transfer (XAT) process further undergoes an intramolecular 1,5-HAT event to generate α-amido alkyl radical, which then intercepted with either cobalt or a reduced cyano arene leads dehydrogenated heteroarylated products, respectively, in good yields.

Language: Английский

Minisci C–H Alkylation of Heterocycles with Unactivated Alkyl Iodides Enabled by Visible Light Photocatalysis DOI
Girish Suresh Yedase,

Ruveen Murgeshan,

Veera Reddy Yatham

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 27, 2025

In this work, we developed a general catalytic strategy that allows Minisci C-H alkylation of variety heterocycles using unactivated alkyl halide as an radical source under visible light photocatalysis. Mild reaction conditions, employing 4CzIPN organophotocatalyst and aerial oxygen green terminal oxidant, broad scope, good functional group tolerance, late-stage bioactive pharmaceutically relevant molecules are advantages the protocol. Preliminary mechanistic studies indicate involvement α-amino further our conditions.

Language: Английский

Citations

0
Substrate-Photocatalyst Reactivity Matching Enables Broad Aryl Halide Scope in Light-Driven, Reductive Cross-Electrophile Coupling Using 13C NMR as a Predictor DOI
Cameron H. Chrisman,

W. Zachary Elder,

Graham C. Haug

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 8103 - 8113

Published: May 1, 2025

Language: Английский

Citations

0
Recent Advances in Strategies for Halide Atom Transfer (XAT) and Their Applications DOI

Yifeng Jiang,

Yanli Yin, Zhiyong Jiang

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(6), P. 1733 - 1733

Published: Jan. 1, 2024

Language: Английский

Citations

2
Synthetic Routes to Access Dicarbonylated Aryls and Heteroaryls DOI
Swadhin Swaraj Acharya, Bibhuti Bhusan Parida

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

The regioselective 1,2-dicarbonylation of aryls and heteroaryls offers access to functionalized dicarbonylated heteroaryls, which opens pharmaceuticals bioactive molecules with diverse synthetic utility.

Language: Английский

Citations

2
α-C(sp3)–H (Hetero)Arylation of Thioethers Enabled by Photoexcited Triplet Ketone Catalysis DOI

Akash Bisoyi,

Alisha Rani Tripathy,

Amit Behera

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(17), P. 12540 - 12546

Published: Aug. 20, 2024

We report herein α-C(sp3)–H (hetero)arylation of thioethers enabled by dual nickel and photoexcited triplet ketone catalysis. The mild reaction conditions this protocol tolerate a variety functional groups further facilitate the late-stage functionalization biologically relevant molecules to afford corresponding products in moderate good yields. Preliminary mechanistic studies suggest that generation α-thioalkyl radical takes place through hydrogen atom transfer (HAT) event, which is involved rate-limiting step cycle, with Ni(0)Ln catalyst followed oxidative addition aryl bromide dominating pathway. Furthermore, heteroaromatic benzylic can also be achieved from reduced 4-cyano pyridine derivatives presence radical–radical coupling without metal. increased yield DABCO might indicate higher rate formation HAT event cation.

Language: Английский

Citations

1
Chemoselective Dehydrogenation and Hetero-Arylation of Amides via Radical Translocation Enabled by Photoexcited Triplet Ketone Catalysis DOI

Akash Bisoyi,

Amit Behera,

Alisha Rani Tripathy

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 16, 2024

We herein report the chemoselective dehydrogenation and heteroarylation of amides through photoexcited triplet ketone catalysis. Under mild reaction conditions, generated aryl radical halogen atom transfer (XAT) process further undergoes an intramolecular 1,5-HAT event to generate α-amido alkyl radical, which then intercepted with either cobalt or a reduced cyano arene leads dehydrogenated heteroarylated products, respectively, in good yields.

Language: Английский

Citations

0