Pd(II)‐catalyzed, Picolinamide‐aided sp<sup>2</sup> γ−C−H Functionalization of Phenylglycinol: Access to γ−C−H Arylated, Alkylated and Halogenated Phenylglycinol Scaffolds

Singh, Prabhakar; Babu, Srinivasarao Arulananda; Aggarwal, Yashika; Patel, Pooja

doi:10.1002/ajoc.202000560

Cited by 9 publications

(2 citation statements)

References 67 publications

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“…All the yields reported are isolated yields and the yields are not optimized and sometimes there is marginal variation in yields and enantiomeric ratio for the corresponding racemic/enantiopure pairs, this is perhaps based on the collection of pure fractions from the column chromatography based on the TLC and also may be due to inadvertent handling/processing errors of samples. Starting materials used in this work to carry out the Pd(II)‐catalyzed γ ‐C(sp 2 )−H alkoxylation with alcohols are known in the literature (see the supporting information) [12h,i] …”

Section: Methodsmentioning

confidence: 99%

“…A literature survey on the Pd(II)‐catalyzed DG‐aided ortho γ ‐C(sp 2 )−H functionalization of enantiopure α ‐alkylbenzylamine derivatives revealed that limited examples of alkylation, alkynylation, carbonylative cyclization, etc have been documented [12] . Along this line, we recently reported the Pd(II)‐catalyzed picolinamide‐aided ortho ‐C−H arylation/alkylation/halogenation of racemic and enantiopure α ‐methylbenzylamine and phenylglycinol scaffolds involving C−C, C−Br and C−I bond‐forming reactions [12h,i] …”

Section: Introductionmentioning

confidence: 99%

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

et al. 2022

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

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

et al. 2022

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

Dalal,

Babu,

Banga

2023

Asian J Org Chem

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

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

2023

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This paper describes the Pd(II)‐catalyzed, picolinamide‐directing‐group‐aided C(sp2)−H (ortho) functionalization of racemic and enantiopure β‐phenylalanines and 3‐amino‐3‐phenylpropanols (1,3‐amino alcohols). The C(sp2)−H (ortho) functionalizations including arylation, bromination, iodination, and alkoxylation were attempted. The C(sp2)−H (ortho) arylation reactions gave biaryl or terphenyl‐type β‐phenylalanine scaffolds, halogenation and methoxylation reactions gave ortho C−H halogenated or methoxylated β‐phenylalanines. Additionally, the C−H arylation of an ortho‐methyl substituted β‐phenylalanine containing both C(sp2)−H and remote C(sp3)−H bonds was investigated. β‐Phenylalanine is an arylated β‐amino acid motif present in various natural products, bioactive molecules, and β‐peptides and it is a precursor to medicinally active compounds. Accordingly, this work contributes to the expansion of the library of unnatural β‐phenylalanine (β‐amino acid) derivatives through site‐selective C−H functionalization.

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Pd(II)‐catalyzed, Picolinamide‐aided sp² γ−C−H Functionalization of Phenylglycinol: Access to γ−C−H Arylated, Alkylated and Halogenated Phenylglycinol Scaffolds

Cited by 9 publications

References 67 publications

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

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

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

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

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Pd(II)‐catalyzed, Picolinamide‐aided sp2 γ−C−H Functionalization of Phenylglycinol: Access to γ−C−H Arylated, Alkylated and Halogenated Phenylglycinol Scaffolds

Cited by 9 publications

References 67 publications

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

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

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

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

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Pd(II)‐catalyzed, Picolinamide‐aided sp² γ−C−H Functionalization of Phenylglycinol: Access to γ−C−H Arylated, Alkylated and Halogenated Phenylglycinol Scaffolds

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

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

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