Utility of 4‐Amino‐2,1,3‐benzothiadiazole Directing Group in the Pd(II)‐catalyzed Arylation of γ‐C−H Bonds of Carboxamides and β‐C‐H Bonds of Amino Acid Carboxamides DOI
Narendra Bisht, Srinivasarao Arulananda Babu, Radha Tomar

et al.

Asian Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 11(12)

Published: Nov. 17, 2022

Abstract Expanding the availability, scope, and limitations of directing groups (DGs) for executing site‐selective C−H activation functionalization substrate scope development are valuable efforts. This paper reports extension utility 4‐amino‐2,1,3‐benzothiadiazole (ABTD) group in Pd(II)‐catalyzed arylation remote sp 2 /sp 3 γ‐C−H bonds aromatic carboxamides β ‐C−H amino acid carboxamides. The performance ABTD DG was compared with other known DGs. For example, we have observed that mono methyl alanine carboxamide possessing iodopyridine yielded pyridylalanine derivative. Conversely, same reaction using 8‐AQ did not yield expected Furthermore, 2,1,3‐benzothiadiazole moiety‐containing compounds an important class molecules materials chemistry medicinally relevant molecules. While this work reveals as including derivatives. On hand, indirectly process ABTD‐aided reactions has enabled to accomplish synthesis a library moiety containing new

Language: Английский

Nickel-Catalyzed Decarbonylative Reductive Alkylation of Aroyl Fluorides with Alkyl Bromides DOI
Qiang Chen,

Jingwen You,

Tian Tian

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(50), P. 9259 - 9263

Published: Dec. 14, 2022

This paper describes the nickel-catalyzed reductive alkylation of aroyl fluorides with alkyl bromides in a decarbonylative manner. In this reaction, various functional groups are well tolerated and C(sp2)-C(sp3) bond can be constructed directly without use organometallic reagents. The present reaction is cross-electrophile coupling via radical pathway, affording corresponding alkylarenes moderate to good yields.

Language: Английский

Citations

16

Construction of carbazole-based unnatural amino acid scaffolds via Pd(ii)-catalyzed C(sp3)–H functionalization DOI
Ramandeep Kaur,

Shefali Banga,

Srinivasarao Arulananda Babu

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(21), P. 4391 - 4414

Published: Jan. 1, 2022

Synthesis of racemic and enantiopure carbazole-based unnatural amino acid motifs was accomplished via diastereoselective Pd( ii )-catalyzed β-C(sp 3 )–H functionalization.

Language: Английский

Citations

15

Pd‐Catalyzed Arylation and Benzylation of Tyrosine at the δ−C(sp2)−H and C(2) Positions: Expanding the Library of Unnatural Tyrosines DOI
Prabhakar Singh, Srinivasarao Arulananda Babu

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(31)

Published: June 20, 2023

Abstract This paper describes Pd(II)‐catalyzed picolinamide‐directed intermolecular arylation and benzylation of remote δ −C(sp 2 )−H bond (C(2) position) the aryl ring in tyrosine derivatives expansion library unnatural tyrosine. Various racemic enantiopure bis C(2) ( ortho C−H) arylated benzylated were assembled good yields. Removal picolinoyl moiety after C(2)−H assembling tyrosine‐based peptides using tyrosines shown. Tyrosine biaryl amino acids are vital scaffolds medicinal chemistry. Correspondingly, this work is a contribution towards with biaryl‐ or terphenyl diarylmethane‐based scaffolds.

Language: Английский

Citations

9

Copper‐Catalyzed Fluoroamide‐Directed Remote C(sp3)‐H Bond Functionalization Through Intramolecular Hydrogen Atom Transfer DOI
Xin Lv, Yuhao Yang, Liejin Zhou

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(13)

Published: Feb. 15, 2024

Abstract Direct C−H functionalization is an important strategy for the rapid synthesis of valuable organic molecules. Radical‐involved remote C(sp 3 )‐H based on hydrogen atom transfer (HAT) becomes method enabling selective direct transformation bonds at specific distal position(s). In recent years, copper‐catalyzed fluoroamide‐directed bond through intramolecular HAT has served as a robust and elegant assembly variety functionalized (sulfon)amides related derivatives. This review focuses advances in this area. These transformations proceed effectively with high selectivities good functional group compatibility under mild conditions.

Language: Английский

Citations

3

4-Aminobenzotriazole Directed Palladium-Catalyzed C-H Acetoxylation and Intramolecular Amination Reaction DOI
Zhuo Wang, Chengqian Li, Yupeng Fan

et al.

Tetrahedron, Journal Year: 2025, Volume and Issue: unknown, P. 134470 - 134470

Published: Jan. 1, 2025

Language: Английский

Citations

0

Palladium-Catalyzed Intermolecular Functionalization of Unactivated Methylene C(sp3)—H Bonds DOI

Ming-Shun Mei,

Yanghui Zhang

Chinese Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 45(2), P. 620 - 620

Published: Jan. 1, 2025

Language: Английский

Citations

0

Insights into the mechanism of 3d transition-metal-catalyzed directed C(sp3)–H bond functionalization reactions DOI Creative Commons

Andrés García‐Viada,

Juan C. Carretero, Javier Adrio

et al.

Chemical Society Reviews, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

This review provides an overview of the research advaces in Ni-, Cu-, Fe- and Co-catalyzed directed C(sp 3 )–H bond functionalization reactions; including design principles, mechanistic discussions, along with potential applications limitations.

Language: Английский

Citations

0

Construction of Biaryl Sulfonamides via Pd(II)-Catalyzed Cross-Coupling of C(sp2)-H Bonds with Iodobenzenesulfonamides DOI Creative Commons

Debabrata Bhattacharya,

S. C. Pal,

Indranil Banerjee

et al.

ACS Omega, Journal Year: 2025, Volume and Issue: unknown

Published: April 21, 2025

This study describes the utility of Pd(II)-catalyzed C-H arylation benzamides for constructing biaryl sulfonamides. Sulfonamides are known their promising applications in pharmaceuticals and agrochemicals. A literature review revealed that sulfonamides were generally constructed via traditional cross-coupling reactions. We report a progressive method obtaining bidentate directing group (8-aminoquinoline or picolinamide)-assisted sp2 bonds aromatic carboxamides with iodobenzenesulfonamides. After reactions, we attempted removal 8-aminoquinoline from synthesized scaffolds possessing carboxamide sulfonamide moieties using triflic acid. In some cases, observed occurrence decarboxylation Friedel-Crafts acylation, affording interesting moiety. The current work contributes toward developing alternative ways assembling various

Language: Английский

Citations

0

Picolinamide-assisted ortho-C–H functionalization of pyrenylglycine derivatives using aryl iodides DOI
Arup Dalal,

Subhankar Bodak,

Srinivasarao Arulananda Babu

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(6), P. 1279 - 1298

Published: Jan. 1, 2024

Chemical transformations involving pyrenylglycine are seldom known. This paper reports the synthesis of C(2)-arylated (an unnatural amino acid) motifs via a Pd( ii )-catalyzed C–H functionalization and arylation in non-K-region pyrene.

Language: Английский

Citations

3

Expanding the Utility of Inexpensive Pyridine‐N‐oxide Directing Group for the Site‐selective sp2/sp3γ‐C−H and sp2δ‐C−H Functionalization of Carboxamides DOI
Radha Tomar, Amit Kumar, Arup Dalal

et al.

Asian Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 11(9)

Published: July 8, 2022

Abstract We have shown our efforts toward expanding the utility of relatively inexpensive pyridine‐ N ‐oxide directing group in Pd(II)‐catalyzed site‐selective γ ‐C(sp 2 )−H, 3 )−H and δ functionalization. The functionalization β −C−H bonds using bidentate (DG) which operates through N,O ‐coordination mode has been well documented literature. However, there exist rare reports dealing with remote sp /sp ‐ δ‐ C−H carboxamides assisted by groups operating via ‐coordination. In this paper, scope DG was examined for accomplishing (mono) arylation substrates containing competitive C(sp bonds. investigation enabled to assemble a library ‐oxide‐based biarylacetamides, heteroaryl‐based biaryl carboxamides, tricyclic quinolones, arylheteroarylmethanes, biaryl‐based aliphatic mono ( ortho ) arylated phenylglycine derivatives. general, derivatives particular, arylacetamide, arylacetic acid (2‐aminopyridyl) motifs are medicinally relevant classes compounds. This work assembling above‐mentioned types compounds group‐aided γ‐ carboxamides.

Language: Английский

Citations

12