Ligand-Enabled δ-C(sp3)−H Borylation of Aliphatic Amines

Hediyala B. Chandrashekar; Pravas Dolui; Bijin Li; Astam Mandal; Hao Liu; Srimanta Guin; Haibo Ge; Debabrata Maiti

doi:10.1002/anie.202105204

Ligand-Enabled δ-C(sp³)−H Borylation of Aliphatic Amines

Hediyala B. Chandrashekar, Pravas Dolui, Bijin Li, Astam Mandal, Hao Liu, Srimanta Guin, Haibo Ge, Debabrata Maiti

Chemistry and Biochemistry

Research output: Contribution to journal › Article › peer-review

18 Scopus citations

Abstract

Directed C−H functionalization has been realized as a complimentary technique to achieve borylation at a distal position of aliphatic amines. Here, we demonstrated the oxidative borylation at the distal δ-position of aliphatic amines using various borylating agents, a palladium catalyst, and a rightly tuned ligand in the presence of a cheap oxidant. Moreover, an organopalladium δ-C(sp³)-H-activated intermediate has been isolated and crystallographically characterized to get mechanistic insight.

Original language	English
Pages (from-to)	18194-18200
Number of pages	7
Journal	Angewandte Chemie - International Edition
Volume	60
Issue number	33
DOIs	https://doi.org/10.1002/anie.202105204
State	Published - Aug 9 2021

Keywords

C−H activation
Pd catalysis
mechanistic studies
δ-borylation

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title = "Ligand-Enabled δ-C(sp3)−H Borylation of Aliphatic Amines",

abstract = "Directed C−H functionalization has been realized as a complimentary technique to achieve borylation at a distal position of aliphatic amines. Here, we demonstrated the oxidative borylation at the distal δ-position of aliphatic amines using various borylating agents, a palladium catalyst, and a rightly tuned ligand in the presence of a cheap oxidant. Moreover, an organopalladium δ-C(sp3)-H-activated intermediate has been isolated and crystallographically characterized to get mechanistic insight.",

keywords = "C−H activation, Pd catalysis, mechanistic studies, δ-borylation",

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T1 - Ligand-Enabled δ-C(sp3)−H Borylation of Aliphatic Amines

AU - Chandrashekar, Hediyala B.

AU - Dolui, Pravas

AU - Li, Bijin

AU - Mandal, Astam

AU - Liu, Hao

AU - Guin, Srimanta

AU - Ge, Haibo

AU - Maiti, Debabrata

PY - 2021/8/9

Y1 - 2021/8/9

N2 - Directed C−H functionalization has been realized as a complimentary technique to achieve borylation at a distal position of aliphatic amines. Here, we demonstrated the oxidative borylation at the distal δ-position of aliphatic amines using various borylating agents, a palladium catalyst, and a rightly tuned ligand in the presence of a cheap oxidant. Moreover, an organopalladium δ-C(sp3)-H-activated intermediate has been isolated and crystallographically characterized to get mechanistic insight.

AB - Directed C−H functionalization has been realized as a complimentary technique to achieve borylation at a distal position of aliphatic amines. Here, we demonstrated the oxidative borylation at the distal δ-position of aliphatic amines using various borylating agents, a palladium catalyst, and a rightly tuned ligand in the presence of a cheap oxidant. Moreover, an organopalladium δ-C(sp3)-H-activated intermediate has been isolated and crystallographically characterized to get mechanistic insight.

KW - C−H activation

KW - Pd catalysis

KW - mechanistic studies

KW - δ-borylation

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U2 - 10.1002/anie.202105204

DO - 10.1002/anie.202105204

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AN - SCOPUS:85109754867

SN - 1433-7851

VL - 60

SP - 18194

EP - 18200

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 33

ER -

Ligand-Enabled δ-C(sp³)−H Borylation of Aliphatic Amines

Abstract

Keywords

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