The Viability of C5‐Protonated‐ and C4,C5‐Ditopic Carbanionic Abnormal NHCs: A New Dimension in NHC Chemistry

The Viability of C5‐Protonated‐ and C4,C5‐Ditopic Carbanionic Abnormal NHCs: A New... The first C5‐protonated abnormal N‐heterocyclic carbene (aNHC), PhC{N(2,6‐iPr2C6H3)}2CHC: (4) is readily accessible by C4‐deprotonation of [ArC{N(2,6‐iPr2C6H3)}2CHCH]X (3 a‐X) (Ar=Ph, X=Br or I) with a base. The aNHC 4 is stable at 298 K in [D8]THF solution and has been spectroscopically characterized. The facile availability of 4 enables the synthesis of a series of main‐group compounds as well as transition‐metal complexes featuring a new phosphorus‐aNHC hybrid ligand. Double deprotonation of [ArC{N(2,6‐iPr2C6H3)}2CHCH]X (Ar=Ph, 3 a‐X (X=Br or I); 4‐Tol, 3 b‐Br; 4‐DMP, 3 c‐Br; Tol=MeC6H4, DMP=Me2NC6H4) with nBuLi yields the C4,C5‐ditopic carbanionic aNHCs, [ArC{N(2,6‐iPr2C6H3)}2(C:)2]Li(THF)n (Ar=Ph, 13 a; 4‐Tol, 13 b; 4‐DMP, 13 c), which on treatment with Ph2PCl affords cationic vicinal bisphosphine derivatives [ArC{N(2,6‐iPr2C6H3)}2{C(PPh2}2]X (Ar=Ph, 14 a‐X, X=Br or I; 4‐Tol, 14 b‐Br; 4‐DMP, 14 c‐Br). http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Chemistry - A European Journal Wiley

The Viability of C5‐Protonated‐ and C4,C5‐Ditopic Carbanionic Abnormal NHCs: A New Dimension in NHC Chemistry

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Publisher
Wiley Subscription Services, Inc., A Wiley Company
Copyright
© 2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
ISSN
0947-6539
eISSN
1521-3765
D.O.I.
10.1002/chem.201800260
Publisher site
See Article on Publisher Site

Abstract

The first C5‐protonated abnormal N‐heterocyclic carbene (aNHC), PhC{N(2,6‐iPr2C6H3)}2CHC: (4) is readily accessible by C4‐deprotonation of [ArC{N(2,6‐iPr2C6H3)}2CHCH]X (3 a‐X) (Ar=Ph, X=Br or I) with a base. The aNHC 4 is stable at 298 K in [D8]THF solution and has been spectroscopically characterized. The facile availability of 4 enables the synthesis of a series of main‐group compounds as well as transition‐metal complexes featuring a new phosphorus‐aNHC hybrid ligand. Double deprotonation of [ArC{N(2,6‐iPr2C6H3)}2CHCH]X (Ar=Ph, 3 a‐X (X=Br or I); 4‐Tol, 3 b‐Br; 4‐DMP, 3 c‐Br; Tol=MeC6H4, DMP=Me2NC6H4) with nBuLi yields the C4,C5‐ditopic carbanionic aNHCs, [ArC{N(2,6‐iPr2C6H3)}2(C:)2]Li(THF)n (Ar=Ph, 13 a; 4‐Tol, 13 b; 4‐DMP, 13 c), which on treatment with Ph2PCl affords cationic vicinal bisphosphine derivatives [ArC{N(2,6‐iPr2C6H3)}2{C(PPh2}2]X (Ar=Ph, 14 a‐X, X=Br or I; 4‐Tol, 14 b‐Br; 4‐DMP, 14 c‐Br).

Journal

Chemistry - A European JournalWiley

Published: Jan 12, 2018

Keywords: ; ; ; ;

References

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