Aluminum-centered C-C Heterocoupling of Organonitriles

Alannah C. M. Thomas; Estelle Bouchat; Kyle G. Pearce; Louis J. Morris; Rex S. C. Charman; Michael S. Hill

doi:10.1021/acs.organomet.5c00335

Aluminum-centered C-C Heterocoupling of Organonitriles

Alannah C. M. Thomas, Estelle Bouchat, Kyle G. Pearce, Louis J. Morris, Rex S. C. Charman, Michael S. Hill

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

Abstract

The C-tert-butyl substituted azacyclopropenylaluminate, [(SiNDipp)Al-η2-{NCt-Bu}K]∞ (SiNDipp = (CH2SiMe2NDipp)2) reacts with both aryl- and alkyl-substituted nitriles. In contrast to previously reported attempts to effect C–C bond formation between two dissimilar nitriles, these reactions enable the completely discriminating heterocoupling of t-BuCN to provide diazabutadienylaluminate dianions that bear two differentiated N═C substituents.

Original language	English
Pages (from-to)	2369–2373
Number of pages	5
Journal	Organometallics
Volume	44
Issue number	20
Early online date	10 Oct 2025
DOIs	https://doi.org/10.1021/acs.organomet.5c00335
Publication status	Published - 27 Oct 2025

Funding

Funders	Funder number
Engineering and Physical Sciences Research Council	EP/R020752/1

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10.1021/acs.organomet.5c00335Licence: CC BY

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title = "Aluminum-centered C-C Heterocoupling of Organonitriles",

abstract = "The C-tert-butyl substituted azacyclopropenylaluminate, [(SiNDipp)Al-η2-\{NCt-Bu\}K]∞ (SiNDipp = (CH2SiMe2NDipp)2) reacts with both aryl- and alkyl-substituted nitriles. In contrast to previously reported attempts to effect C–C bond formation between two dissimilar nitriles, these reactions enable the completely discriminating heterocoupling of t-BuCN to provide diazabutadienylaluminate dianions that bear two differentiated N═C substituents.",

author = "Thomas, \{Alannah C. M.\} and Estelle Bouchat and Pearce, \{Kyle G.\} and Morris, \{Louis J.\} and Charman, \{Rex S. C.\} and Hill, \{Michael S.\}",

year = "2025",

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day = "27",

doi = "10.1021/acs.organomet.5c00335",

language = "English",

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T1 - Aluminum-centered C-C Heterocoupling of Organonitriles

AU - Thomas, Alannah C. M.

AU - Bouchat, Estelle

AU - Pearce, Kyle G.

AU - Morris, Louis J.

AU - Charman, Rex S. C.

AU - Hill, Michael S.

PY - 2025/10/27

Y1 - 2025/10/27

N2 - The C-tert-butyl substituted azacyclopropenylaluminate, [(SiNDipp)Al-η2-{NCt-Bu}K]∞ (SiNDipp = (CH2SiMe2NDipp)2) reacts with both aryl- and alkyl-substituted nitriles. In contrast to previously reported attempts to effect C–C bond formation between two dissimilar nitriles, these reactions enable the completely discriminating heterocoupling of t-BuCN to provide diazabutadienylaluminate dianions that bear two differentiated N═C substituents.

AB - The C-tert-butyl substituted azacyclopropenylaluminate, [(SiNDipp)Al-η2-{NCt-Bu}K]∞ (SiNDipp = (CH2SiMe2NDipp)2) reacts with both aryl- and alkyl-substituted nitriles. In contrast to previously reported attempts to effect C–C bond formation between two dissimilar nitriles, these reactions enable the completely discriminating heterocoupling of t-BuCN to provide diazabutadienylaluminate dianions that bear two differentiated N═C substituents.

U2 - 10.1021/acs.organomet.5c00335

DO - 10.1021/acs.organomet.5c00335

M3 - Article

SN - 0276-7333

VL - 44

SP - 2369

EP - 2373

JO - Organometallics

JF - Organometallics

IS - 20

ER -

Aluminum-centered C-C Heterocoupling of Organonitriles

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