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A simple, broad-scope nickel(0) precatalyst system for direct amination of allyl alcohols

Research output: Contribution to Journal/Magazine › Journal article › peer-review

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A simple, broad-scope nickel(0) precatalyst system for direct amination of allyl alcohols. / Sweeney, Joseph B.; Ball, Anthony; Lawrence, Philippa et al.
In: Angewandte Chemie International Edition, Vol. 57, No. 32, 06.08.2018, p. 10202-10206.

Research output: Contribution to Journal/Magazine › Journal article › peer-review

Harvard

Sweeney, JB, Ball, A, Lawrence, P, Sinclair, M & Smith, L 2018, 'A simple, broad-scope nickel(0) precatalyst system for direct amination of allyl alcohols', Angewandte Chemie International Edition, vol. 57, no. 32, pp. 10202-10206. https://doi.org/10.1002/anie.201805611

APA

Sweeney, J. B., Ball, A., Lawrence, P., Sinclair, M., & Smith, L. (2018). A simple, broad-scope nickel(0) precatalyst system for direct amination of allyl alcohols. Angewandte Chemie International Edition, 57(32), 10202-10206. https://doi.org/10.1002/anie.201805611

Vancouver

Sweeney JB, Ball A, Lawrence P, Sinclair M, Smith L. A simple, broad-scope nickel(0) precatalyst system for direct amination of allyl alcohols. Angewandte Chemie International Edition. 2018 Aug 6;57(32):10202-10206. Epub 2018 Jul 12. doi: 10.1002/anie.201805611

Author

Sweeney, Joseph B. ; Ball, Anthony ; Lawrence, Philippa et al. / A simple, broad-scope nickel(0) precatalyst system for direct amination of allyl alcohols. In: Angewandte Chemie International Edition. 2018 ; Vol. 57, No. 32. pp. 10202-10206.

Bibtex

@article{e56b6cf2c3ab4b09a5d16e23037aacab,
title = "A simple, broad-scope nickel(0) precatalyst system for direct amination of allyl alcohols",
abstract = "The preparation of allylic amines is traditionally accomplished by reactions of amines with reactive electrophiles, such as allylic halides, sulfonates, or oxyphosphonium species; such methods involve hazardous reagents, generate stoichiometric waste streams, and often suffer from side reactions (such as overalkylation). We report here the first broad‐scope nickel‐catalysed direct amination of allyl alcohols: An inexpensive NiII/Zn couple enables the allylation of primary, secondary, and electron‐deficient amines without the need for glove‐box techniques. Under mild conditions, primary and secondary aliphatic amines react smoothly with a range of allyl alcohols, giving secondary and tertiary amines efficiently. This “totally catalytic” method can also be applied to electron‐deficient nitrogen nucleophiles; the practicality of the process was demonstrated in an efficient, gram‐scale preparation of the calcium antagonist drug substance flunarizine (Sibelium{\textregistered}).",
keywords = "allylation, amination , CN bond formation, nickel, sustainable chemistry",
author = "Sweeney, {Joseph B.} and Anthony Ball and Philippa Lawrence and Mackenzie Sinclair and Luke Smith",
year = "2018",
month = aug,
day = "6",
doi = "10.1002/anie.201805611",
language = "English",
volume = "57",
pages = "10202--10206",
journal = "Angewandte Chemie International Edition",
issn = "1433-7851",
publisher = "Wiley-VCH Verlag",
number = "32",

}

RIS

TY - JOUR

T1 - A simple, broad-scope nickel(0) precatalyst system for direct amination of allyl alcohols

AU - Sweeney, Joseph B.

AU - Ball, Anthony

AU - Lawrence, Philippa

AU - Sinclair, Mackenzie

AU - Smith, Luke

PY - 2018/8/6

Y1 - 2018/8/6

N2 - The preparation of allylic amines is traditionally accomplished by reactions of amines with reactive electrophiles, such as allylic halides, sulfonates, or oxyphosphonium species; such methods involve hazardous reagents, generate stoichiometric waste streams, and often suffer from side reactions (such as overalkylation). We report here the first broad‐scope nickel‐catalysed direct amination of allyl alcohols: An inexpensive NiII/Zn couple enables the allylation of primary, secondary, and electron‐deficient amines without the need for glove‐box techniques. Under mild conditions, primary and secondary aliphatic amines react smoothly with a range of allyl alcohols, giving secondary and tertiary amines efficiently. This “totally catalytic” method can also be applied to electron‐deficient nitrogen nucleophiles; the practicality of the process was demonstrated in an efficient, gram‐scale preparation of the calcium antagonist drug substance flunarizine (Sibelium®).

AB - The preparation of allylic amines is traditionally accomplished by reactions of amines with reactive electrophiles, such as allylic halides, sulfonates, or oxyphosphonium species; such methods involve hazardous reagents, generate stoichiometric waste streams, and often suffer from side reactions (such as overalkylation). We report here the first broad‐scope nickel‐catalysed direct amination of allyl alcohols: An inexpensive NiII/Zn couple enables the allylation of primary, secondary, and electron‐deficient amines without the need for glove‐box techniques. Under mild conditions, primary and secondary aliphatic amines react smoothly with a range of allyl alcohols, giving secondary and tertiary amines efficiently. This “totally catalytic” method can also be applied to electron‐deficient nitrogen nucleophiles; the practicality of the process was demonstrated in an efficient, gram‐scale preparation of the calcium antagonist drug substance flunarizine (Sibelium®).

KW - allylation

KW - amination

KW - CN bond formation

KW - nickel

KW - sustainable chemistry

U2 - 10.1002/anie.201805611

DO - 10.1002/anie.201805611

M3 - Journal article

VL - 57

SP - 10202

EP - 10206

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

SN - 1433-7851

IS - 32

ER -