Synthesis of N -heterocyclic carbene boranes via silver N -heterocyclic carbene complexes

Ono, S.; Watanabe, Takashi; Nakamura, Yosuke; Sato, Hiroyasu; Hashimoto, Toru; Yamaguchi, Yoshitaka

doi:10.1016/j.poly.2017.08.045

Cited by 3 publications

(1 citation statement)

References 55 publications

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“…Under analogous reaction conditions, metalation of [ BBN H 2 CNC][BPh 4 ] 2 did not afford a tractable iron-containing species; instead, an inert Lewis acid/base pair formed between the free carbene and acidic 9-BBN (Figure ). The identity of the quenched adduct was confirmed by independent deprotonation of [ BBN H 2 CNC][BPh 4 ] 2 with n BuLi, which afforded a tetrahedral 11 B NMR resonance at −15.44 ppm (C 6 D 6 ), similar to that for the Me NHC Mes ·BEt 3 adduct (−13.1 ppm, C 6 D 6 ) …”

Section: Results and Discussionmentioning

confidence: 80%

Requirements for Lewis Acid-Mediated Capture and N–N Bond Cleavage of Hydrazine at Iron

2019

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An iron complex bearing a pyridine(dicarbene) pincer was designed to probe the requirements of Lewis acid enabled N 2 H 4 capture and subsequent N-N bond cleavage. Appended boron Lewis acids were installed by two methods to circumvent the incompatibilities associated with Lewis acid/base quenching of free carbenes and boranes. N 2 H 4 capture by borane Lewis acids is dependent on both Lewis acidity and the steric profile about boron. A substitutionally inert primary coordination sphere at iron prevents an Fe-N 2 H 4 interaction as well as N-N bond homolysis upon reduction.

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Section: Results and Discussionmentioning

confidence: 80%

Requirements for Lewis Acid-Mediated Capture and N–N Bond Cleavage of Hydrazine at Iron

2019

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MeOH‐Mediated Efficient Reduction with N‐Heterocyclic Carbene Boranes Towards the Synthesis of Cyclic Sulfamates and Sulfonamides

Zheng,

Song,

Guan

et al. 2023

ChemistrySelect

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An efficient approach for the reduction of cyclic N‐sulfonylimines using N‐heterocyclic carbene boranes as the hydride donor was developed, leading to various cyclic sulfamates and sulfonamides in excellent yields. The approach had broad scope including both the N‐sulfonyl aldimines and ketimines under mild reaction conditions, which proves that the NHC‐boranes are good alternatives as the reductive reagents.

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The key role of R–NHC coupling (R = C, H, heteroatom) and M–NHC bond cleavage in the evolution of M/NHC complexes and formation of catalytically active species

et al. 2020

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Synthesis of N -heterocyclic carbene boranes via silver N -heterocyclic carbene complexes

Cited by 3 publications

References 55 publications

Requirements for Lewis Acid-Mediated Capture and N–N Bond Cleavage of Hydrazine at Iron

Requirements for Lewis Acid-Mediated Capture and N–N Bond Cleavage of Hydrazine at Iron

MeOH‐Mediated Efficient Reduction with N‐Heterocyclic Carbene Boranes Towards the Synthesis of Cyclic Sulfamates and Sulfonamides

The key role of R–NHC coupling (R = C, H, heteroatom) and M–NHC bond cleavage in the evolution of M/NHC complexes and formation of catalytically active species

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