Assembling of Polyaryls (Terphenyls, Tetraphenyls, Pentaphenyls, and Hexaphenyls) through Pd(II)‐catalyzed C−H Arylation of Biaryl Carboxamides with Iodobiaryls DOI
Arup Dalal, Srinivasarao Arulananda Babu,

Shefali Banga

et al.

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 13(1)

Published: Nov. 21, 2023

Abstract A wide range of polyaryl compounds (π‐extended biaryls) including terphenyls, tetraphenyls, pentaphenyls, and hexaphenyls were assembled in a single operation Pd(II)‐catalyzed C−H coupling biaryl carboxamides iodobiaryls. Traditionally, cross‐coupling protocols involving organometallic reagents employed to assemble the core structure π‐extended biaryls (polyphenylenes or polyaryls). The pre‐assembling is limitation investigations pertaining aryl‐aryl reactions affording polyaryls (polyphenylenes). We report application bidentate directing group (DG)‐aided arylation method for constructing motifs using biaryl‐based iodobiaryls as partners operation. current investigation on DG‐aided with expected serve useful route enrich library

Language: Английский

Unified approaches in transition metal catalyzed C(sp3)–H functionalization: recent advances and mechanistic aspects DOI
Jagrit Grover,

Amal Tom Sebastian,

S.K. Maiti

et al.

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

Published: Jan. 1, 2025

Direct alteration of unactivated C–H bonds organic building blocks.

Language: Английский

Citations

1
LNL-Carbazole Pincer Ligand: More than the Sum of Its Parts DOI Creative Commons
George Kleinhans, Aino J. Karhu, Hugo Boddaert

et al.

Chemical Reviews, Journal Year: 2023, Volume and Issue: 123(13), P. 8781 - 8858

Published: June 23, 2023

The utility of carbazole in photo-, electro-, and medicinal applications has ensured its widespread use also as the backbone tridentate pincer ligands. In this review, aim is to identify illustrate key features LNL-carbazolide binding transition metal centers (with L = flanking donor moieties, e.g., C, N, P, O-groups) a systematic bottom-up progression marked benefits attainable from (i) rigid aromatic scaffold (modulable both 1,8- 3,6-positions), (ii) significant electronic effect central carbazole-amido metal, tunable sterics electronics (iii) L-moieties (iv) wingtip R-groups on L-donors, with their corresponding influence coordination geometry, d-electron configuration, resultant reactivity. Systematic implementation ligand design strategies not isolation, but combinatorial approach, showcased demonstrate potential for functional molecules that are only modulable adaptable wide-ranging (e.g., stereoselective (photo)catalysis, challenging small molecule activation, SET redox applications, even chemotherapeutics) an indication future research efforts anticipated stem versatile assembly, metals s-, p-, f-block elements.

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

8
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
Construction of β‐Phenylalanine Derivatives through Pd‐Catalyzed, C(sp2)−H (ortho) Functionalization DOI

Urja Narang,

Prabhakar Singh, Srinivasarao Arulananda Babu

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(29)

Published: June 13, 2023

Abstract This paper describes the Pd(II)‐catalyzed, picolinamide‐directing‐group‐aided C(sp 2 )−H ( ortho ) functionalization of racemic and enantiopure β ‐phenylalanines 3‐amino‐3‐phenylpropanols (1,3‐amino alcohols). The functionalizations including arylation, bromination, iodination, alkoxylation were attempted. arylation reactions gave biaryl or terphenyl‐type ‐phenylalanine scaffolds, halogenation methoxylation C−H halogenated methoxylated ‐phenylalanines. Additionally, an ‐methyl substituted containing both remote 3 bonds was investigated. ‐Phenylalanine is arylated ‐amino acid motif present in various natural products, bioactive molecules, ‐peptides it a precursor to medicinally active compounds. Accordingly, this work contributes expansion library unnatural acid) derivatives through site‐selective functionalization.

Language: Английский

Citations

7
Pd(ii)-catalyzed selective β-C–H functionalization of azobenzene carboxamides DOI

Rayavarapu Padmavathi,

Srinivasarao Arulananda Babu

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(13), P. 2689 - 2694

Published: Jan. 1, 2023

We report a Pd(II)-catalyzed bidentate directing group 8-aminoquinoline-aided, site-selective β-C-H functionalization protocol for assembling modified azobenzene carboxamides. Considering the importance of azobenzenes in chemical sciences, this paper reports new route enriching library motifs.

Language: Английский

Citations

6
Pd(ii)-catalyzed coupling of C–H bonds of carboxamides with iodoazobenzenes toward modified azobenzenes DOI

Sonam Suwasia,

Sugumar Venkataramani, Srinivasarao Arulananda Babu

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(8), P. 1793 - 1813

Published: Jan. 1, 2023

In this paper, we report a synthetic protocol for the construction of biaryl motif-based or π-extended azobenzene and alkylated derivatives via Pd(II)-catalyzed bidentate directing group (DG)-aided C-H activation functionalization strategy. past, synthesis azobenzenes was accomplished through traditional cross-coupling reaction involving organometallic reagents aryl halides equivalent coupling partners. We have shown direct bonds aromatic/aliphatic carboxamides (possessing DG) with iodoazobenzenes as partners DG-aided, site-selective method. Azobenzene-containing compounds are versatile class photo-responsive molecules that found applications across branches chemical, biological materials sciences prevalent in medicinally relevant molecules. Accordingly, new functionalized azobenzene-based scaffolds has been an attractive topic research. Although classical methods efficient, they need pre-functionalized starting materials. This Pd(II)-catalyzed, group-aided arylation aromatic aliphatic using iodoazobenzene partner affording is additional route also contribution towards enriching library modified azobenzenes. photoswitching properties representative synthesized

Language: Английский

Citations

4
Fluorene and Fluorenone Unnatural Amino Acid Motifs via Diastereoselective Pd(II)‐Catalyzed sp3C−H Functionalization DOI

Shefali Banga,

Srinivasarao Arulananda Babu

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(23)

Published: April 17, 2024

Abstract This paper reports the construction of racemic and enantiopure (D‐ L‐) fluorene fluorenone‐based novel unnatural amino acid derivatives. The Pd(II)‐catalyzed bidentate directing group‐aided arylation prochiral β ‐C(sp 3 )‐H bonds in racemic, carboxamides acids with iodofluorenes was reported. examples fluorenone motifs containing comprising norvaline, leucine, phenylalanine, norleucine, 2‐aminooctanoic derivatives having anti ‐stereochemistry (with good enantiopurity) accomplished. bis fluorenyl alanine scaffolds motif‐containing non‐ α ‐amino (aminoalkanoic acid) also Examples removal group (8‐aminoquinoline) phthalimide‐protecting present fluorenyl‐based have been shown. Accordingly, motif‐based esters free group‐containing were synthesized. stereochemistry major ( ) diastereomers obtained via ascertained from X‐ray structure a representative compound. Fluorene‐ are vital skeletons materials medicinal chemistry research. this work is contribution towards enriching library scaffolds.

Language: Английский

Citations

1
Synthesis of biaryl-based carbazoles via C-H functionalization and exploration of their anticancer activities DOI
Ramandeep Kaur, Haritha Dilip, Sivapriya Kirubakaran

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(45), P. 8916 - 8944

Published: Jan. 1, 2024

We described the application of C–H functionalization for constructing carbazole-based biaryls and their anticancer activities in cancer cell lines, e.g. , HeLa, HCT116, MDA-MB-231 MDA-MB-468 human embryonic kidney line HEK293T.

Language: Английский

Citations

1
Pd(II)‐Catalyzed, γ‐C(sp2)−H Alkoxylation in α‐Methylbenzylamine, Phenylglycinol, 3‐Amino‐3‐Phenylpropanol Toward Enantiopure Aryl Alkyl Ethers DOI

Yashika Aggarwal,

Rayavarapu Padmavathi,

Prabhakar Singh

et al.

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

Published: Aug. 8, 2022

Abstract This paper reports the synthesis of enantiopure aryl alkyl ethers via Pd(II)‐catalyzed picolinamide‐aided γ ‐C(sp 2 )−H alkoxylation various α ‐alkylbenzylamine derivatives using alcohols. Enantiopure ‐methylbenzylamines and amino alcohol substrates such as 2‐amino‐2‐phenylethanol (phenylglycinol) 3‐amino‐3‐phenylpropanol were subjected to (etherification) with alcohols PIDA. ‐Alkylbenzylamines phenylglycinols are valuable building blocks in organic medicinal chemistry research areas. Accordingly, this work has enabled assembling ortho ‐alkoxylated ‐methylbenzylamine containing ether functionality. We have shown utility for ‐methylbenzylamine‐based sulfamoylcarbamates carboxamides which structurally related bio‐active compounds known literature. demonstrates substrate scope elaboration C−H functionalization etherification through C−O bond‐forming process functionality ‐alkylbenzylamines.

Language: Английский

Citations

7