Synthesis of amines via coupling of imines and alkylarenes

Vaishnavi N. Nair; Uttam K. Tambar

doi:10.1016/j.tetlet.2022.153788

Synthesis of amines via coupling of imines and alkylarenes

Vaishnavi N. Nair, Uttam K. Tambar

Research output: Contribution to journal › Review article › peer-review

2 Scopus citations

Abstract

Recent advances in selective C[sbnd]H functionalization have resulted in powerful strategies for the synthesis of important target molecules from petroleum-derived hydrocarbons. In particular, alkylarenes such as toluene and xylenes are abundant feedstock chemicals that are emerging as useful substrates in C[sbnd]C and C[sbnd]X bond forming reactions. We review benzylic C[sbnd]H functionalization of alkylarenes for the synthesis of amines. We focus on the direct coupling of alkylarenes and imines through two distinct modes of activation: heterolytic and homolytic cleavage of benzylic C[sbnd]H bonds.

Original language	English (US)
Article number	153788
Journal	Tetrahedron Letters
DOIs	https://doi.org/10.1016/j.tetlet.2022.153788
State	Accepted/In press - 2022

Keywords

Alkylarene
Amine
C[sbnd]H functionalization
Imine
Photochemistry
Radical

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2022.153788

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title = "Synthesis of amines via coupling of imines and alkylarenes",

abstract = "Recent advances in selective C[sbnd]H functionalization have resulted in powerful strategies for the synthesis of important target molecules from petroleum-derived hydrocarbons. In particular, alkylarenes such as toluene and xylenes are abundant feedstock chemicals that are emerging as useful substrates in C[sbnd]C and C[sbnd]X bond forming reactions. We review benzylic C[sbnd]H functionalization of alkylarenes for the synthesis of amines. We focus on the direct coupling of alkylarenes and imines through two distinct modes of activation: heterolytic and homolytic cleavage of benzylic C[sbnd]H bonds.",

keywords = "Alkylarene, Amine, C[sbnd]H functionalization, Imine, Photochemistry, Radical",

author = "Nair, {Vaishnavi N.} and Tambar, {Uttam K.}",

note = "Funding Information: Financial support was provided by W. W. Caruth, Jr. Endowed Scholarship , Welch Foundation (I-1748), National Institutes of Health ( R01GM102604 ), American Chemical Society Petroleum Research Fund (59177-ND1), Teva Pharmaceuticals Marc A. Goshko Memorial Grant (60011-TEV), and Sloan Research Fellowship . V.N.N. acknowledges the Sarah and Frank McKnight Fund Graduate Fellowship. We also thank our diverse collection of lab members for creating a supportive environment for research. Publisher Copyright: {\textcopyright} 2022 Elsevier Ltd",

year = "2022",

doi = "10.1016/j.tetlet.2022.153788",

language = "English (US)",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

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TY - JOUR

T1 - Synthesis of amines via coupling of imines and alkylarenes

AU - Nair, Vaishnavi N.

AU - Tambar, Uttam K.

N1 - Funding Information: Financial support was provided by W. W. Caruth, Jr. Endowed Scholarship , Welch Foundation (I-1748), National Institutes of Health ( R01GM102604 ), American Chemical Society Petroleum Research Fund (59177-ND1), Teva Pharmaceuticals Marc A. Goshko Memorial Grant (60011-TEV), and Sloan Research Fellowship . V.N.N. acknowledges the Sarah and Frank McKnight Fund Graduate Fellowship. We also thank our diverse collection of lab members for creating a supportive environment for research. Publisher Copyright: © 2022 Elsevier Ltd

PY - 2022

Y1 - 2022

N2 - Recent advances in selective C[sbnd]H functionalization have resulted in powerful strategies for the synthesis of important target molecules from petroleum-derived hydrocarbons. In particular, alkylarenes such as toluene and xylenes are abundant feedstock chemicals that are emerging as useful substrates in C[sbnd]C and C[sbnd]X bond forming reactions. We review benzylic C[sbnd]H functionalization of alkylarenes for the synthesis of amines. We focus on the direct coupling of alkylarenes and imines through two distinct modes of activation: heterolytic and homolytic cleavage of benzylic C[sbnd]H bonds.

AB - Recent advances in selective C[sbnd]H functionalization have resulted in powerful strategies for the synthesis of important target molecules from petroleum-derived hydrocarbons. In particular, alkylarenes such as toluene and xylenes are abundant feedstock chemicals that are emerging as useful substrates in C[sbnd]C and C[sbnd]X bond forming reactions. We review benzylic C[sbnd]H functionalization of alkylarenes for the synthesis of amines. We focus on the direct coupling of alkylarenes and imines through two distinct modes of activation: heterolytic and homolytic cleavage of benzylic C[sbnd]H bonds.

KW - Alkylarene

KW - Amine

KW - C[sbnd]H functionalization

KW - Imine

KW - Photochemistry

KW - Radical

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U2 - 10.1016/j.tetlet.2022.153788

DO - 10.1016/j.tetlet.2022.153788

M3 - Review article

AN - SCOPUS:85130038650

SN - 0040-4039

JO - Tetrahedron Letters

JF - Tetrahedron Letters

M1 - 153788

ER -

Synthesis of amines via coupling of imines and alkylarenes

Abstract

Keywords

ASJC Scopus subject areas

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