Mechanistic development and recent applications of the Chan–Lam amination

Matthew West; James Fyfe; Julien C. Vantourout; Allan J. B. Watson

doi:10.1021/acs.chemrev.9b00491

Mechanistic development and recent applications of the Chan–Lam amination

Matthew West, James Fyfe, Julien C. Vantourout, Allan J. B. Watson

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

299 Citations (Scopus)

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Abstract

Transition metal-mediated formation of C–N bonds is an essential synthetic methodology. The discovery of the Chan–Lam amination provided a C–N bond forming process that was mild, convenient, and inexpensive, offering an alternative to complementary methods using other transition metals (TMs). Over the past 20 years, this reaction has seen considerable development in its scope of application, uptake into industry, and understanding of its mechanism. This review provides an account of the development of the Chan–Lam amination, highlighting progress and notable examples of application since 2011. Focus is given to evolution in mechanistic understanding and selected applications of the methodology within medicinal and process chemistry.

Original language	English
Journal	Chemical Reviews
Volume	Articles ASAP
Early online date	22 Nov 2019
DOIs	https://doi.org/10.1021/acs.chemrev.9b00491
Publication status	E-pub ahead of print - 22 Nov 2019

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Copyright © 2019 American Chemical Society. This work has been made available online in accordance with publisher policies or with permission. Permission for further reuse of this content should be sought from the publisher or the rights holder. This is the author created accepted manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1021/acs.chemrev.9b00491
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title = "Mechanistic development and recent applications of the Chan–Lam amination",

abstract = "Transition metal-mediated formation of C–N bonds is an essential synthetic methodology. The discovery of the Chan–Lam amination provided a C–N bond forming process that was mild, convenient, and inexpensive, offering an alternative to complementary methods using other transition metals (TMs). Over the past 20 years, this reaction has seen considerable development in its scope of application, uptake into industry, and understanding of its mechanism. This review provides an account of the development of the Chan–Lam amination, highlighting progress and notable examples of application since 2011. Focus is given to evolution in mechanistic understanding and selected applications of the methodology within medicinal and process chemistry.",

author = "Matthew West and James Fyfe and Vantourout, {Julien C.} and Watson, {Allan J. B.}",

note = "Authors thank the University of St Andrews for a PhD studentship (MJW), the Leverhulme Trust for a postdoctoral fellowship (grant no.: RPG-2018-362; JWBF).",

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doi = "10.1021/acs.chemrev.9b00491",

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T1 - Mechanistic development and recent applications of the Chan–Lam amination

AU - West, Matthew

AU - Fyfe, James

AU - Vantourout, Julien C.

AU - Watson, Allan J. B.

N1 - Authors thank the University of St Andrews for a PhD studentship (MJW), the Leverhulme Trust for a postdoctoral fellowship (grant no.: RPG-2018-362; JWBF).

PY - 2019/11/22

Y1 - 2019/11/22

N2 - Transition metal-mediated formation of C–N bonds is an essential synthetic methodology. The discovery of the Chan–Lam amination provided a C–N bond forming process that was mild, convenient, and inexpensive, offering an alternative to complementary methods using other transition metals (TMs). Over the past 20 years, this reaction has seen considerable development in its scope of application, uptake into industry, and understanding of its mechanism. This review provides an account of the development of the Chan–Lam amination, highlighting progress and notable examples of application since 2011. Focus is given to evolution in mechanistic understanding and selected applications of the methodology within medicinal and process chemistry.

AB - Transition metal-mediated formation of C–N bonds is an essential synthetic methodology. The discovery of the Chan–Lam amination provided a C–N bond forming process that was mild, convenient, and inexpensive, offering an alternative to complementary methods using other transition metals (TMs). Over the past 20 years, this reaction has seen considerable development in its scope of application, uptake into industry, and understanding of its mechanism. This review provides an account of the development of the Chan–Lam amination, highlighting progress and notable examples of application since 2011. Focus is given to evolution in mechanistic understanding and selected applications of the methodology within medicinal and process chemistry.

U2 - 10.1021/acs.chemrev.9b00491

DO - 10.1021/acs.chemrev.9b00491

M3 - Review article

SN - 0009-2665

VL - Articles ASAP

JO - Chemical Reviews

JF - Chemical Reviews

ER -

Mechanistic development and recent applications of the Chan–Lam amination

Abstract

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