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

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
Rhodium-Catalyzed Regioselective C3Ar Functionalization of Tyrosines with Maleimides and Its Late-Stage Peptide Exemplification DOI

Narendra Dinkar Kharat,

Sushma Naharwal,

Disha Tank

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(42), P. 7673 - 7677

Published: Oct. 19, 2023

Pyridyloxy-directed Rh(III)-catalyzed regioselective C3Ar-H alkenylation of protected tyrosines was achieved with N-aryl and N-alkyl maleimides, furnishing a series maleimide-appended tyrosine-based unnatural amino acids in good yields. Further, the late-stage exemplification strategy successfully accomplished on tyrosine-containing dipeptides, tripeptides, tetrapeptides moderate reactivity. Also, chemical applications were executed toward nailing tyrosine other via maleimide linker intramolecular hydroarylation to produce tyrosine-centered stapled products succinimide-glued macrocyclized products, respectively.

Language: Английский

Citations

4
Metal-free functionalization of tyrosine residues in short peptides and study of the morphological alterations DOI
Santanu Kumar Karmakar,

Genji Sukumar,

Seelam Prasanthkumar

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(28), P. 3802 - 3805

Published: Jan. 1, 2024

An efficient metal-free method for the conversion of tyrosine to 4-amino-3-methoxy phenylalanine or 4-amino has been developed in one pot via controlled oxidative dearomative functionalization.

Language: Английский

Citations

1
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
Iridium-catalyzed diacylmethylation of tyrosines and its peptides with sulfoxonium ylides DOI Creative Commons

Narendra Dinkar Kharat,

Sushma Naharwal,

Siva S. Panda

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(59), P. 7622 - 7625

Published: Jan. 1, 2024

Pyridyloxy-directed Ir( iii )-catalyzed diacylmethylation of protected tyrosines was achieved with alkyl and (hetero)aryl sulfoxonium ylides, furnishing tyrosine-based unnatural amino acids in good yields.

Language: Английский

Citations

0
Pd-Catalyzed Remote δ-C(sp2)–H Functionalization in Phenylalaninol: Expanding the Library of Phenylalaninols DOI
Srinivasarao Arulananda Babu, Prabhakar Singh

Synthesis, Journal Year: 2023, Volume and Issue: 55(24), P. 4113 - 4144

Published: Aug. 2, 2023

Abstract We report the Pd(II)-catalyzed, picolinamide-directed δ-C(sp2)–H (ortho) functionalization of phenylalaninol scaffolds. Assembling δ-C–H arylated, alkylated, benzylated, alkenylated, brominated, and iodinated scaffolds was accomplished. The arylation reaction occurred under neat conditions. Hydrolysis picolinamide moiety synthetic utility arylated substrates were explored. have also shown preparation some modified Matijin–Su (aurantiamide) derivatives using bis compounds obtained from (Matijin–Su is an anti-HBV agent possessing unit). Considering importance phenylalaninols, this work contributes to expanding library demonstrates substrate scope development in remote reactions.

Language: Английский

Citations

0
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

Citations

0