+ Site Statistics
References:
54,258,434
Abstracts:
29,560,870
PMIDs:
28,072,757
+ Search Articles
+ PDF Full Text Service
How our service works
Request PDF Full Text
+ Follow Us
Follow on Facebook
Follow on Twitter
Follow on LinkedIn
+ Subscribe to Site Feeds
Most Shared
PDF Full Text
+ Translate
+ Recently Requested

N-Heterocyclic carbene boranes are good hydride donors



N-Heterocyclic carbene boranes are good hydride donors



Organic Letters 14(1): 82-85



The nucleophilicity parameters (N) of 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene borane and 1,3-dimethylimidazol-2-ylidene borane are 9.55 and 11.88. This places N-heterocyclic carbene boranes (NHC-boranes) among the most nucleophilic classes of neutral hydride donors. Reductions of highly electron-poor C═N and C═C bonds provide hydrogenation products along with new, stable borylated products. The results suggest that NHC-boranes have considerable untapped potential as neutral organic reductants.

Please choose payment method:






(PDF emailed within 0-6 h: $19.90)

Accession: 054528028

Download citation: RISBibTeXText

PMID: 22149270

DOI: 10.1021/ol202836p


Related references

Dynamic Behavior of N-Heterocyclic Carbene Boranes: Boron-Carbene Bonds in B,B-Disubstituted N,N-Dimethylimidazol-2-ylidene Boranes Have Substantial Rotation Barriers. Journal of Organic Chemistry 80(9): 4465-4469, 2015

N-Heterocyclic Carbene Boryl Iodides Catalyze Insertion Reactions of N-Heterocyclic Carbene Boranes and Diazoesters. Organic Letters 19(13): 3680-3683, 2017

N-Heterocyclic Carbene Boranes are Hydrogen Donors in Masamune-Bergman Reactions of Benzo[3,4]cyclodec-3-ene-1,5-diynes. Journal of Organic Chemistry, 2017

Radical Reactions of N-Heterocyclic Carbene Boranes with Organic Nitriles: Cyanation of NHC-Boranes and Reductive Decyanation of Malononitriles. Journal of the American Chemical Society 137(26): 8617-8622, 2015

Reactions of N-heterocyclic carbene boranes with 5-diazo-2,2-dimethyl-1,3-dioxane-4,6-dione: Synthesis of mono- and bis-hydrazonyl NHC-boranes. Journal of Organic Chemistry, 2018

Hydroboration of arynes with N-heterocyclic carbene boranes. Angewandte Chemie 53(48): 13150-4, 2015

Synthesis and reactions of N-heterocyclic carbene boranes. Angewandte Chemie 50(44): 10294-10317, 2011

Ionic and organometallic reductions with N-heterocyclic carbene boranes. Chemistry 15(47): 12937-12940, 2009

Borenium ion catalyzed hydroboration of alkenes with N-heterocyclic carbene-boranes. Journal of the American Chemical Society 134(29): 12281-8, 2012

Metal-free dehydrogenation of amine-boranes by an N-heterocyclic carbene. Dalton Transactions 42(13): 4625-4632, 2013

Radical trans-Hydroboration of Alkynes with N-Heterocyclic Carbene Boranes. Angewandte Chemie, 2018

Diastereoselective Radical Hydrogen Transfer Reactions using N-Heterocyclic Carbene Boranes. Journal of Organic Chemistry 81(22): 11427-11431, 2016

Asymmetric Reduction of tert-Butanesulfinyl Ketimines by N-Heterocyclic Carbene Boranes. Journal of Organic Chemistry 80(22): 11441-6, 2015

Synthesis and Suzuki Reactions of N-Heterocyclic Carbene Difluoro(aryl)-boranes. Organic Letters 17(14): 3394-3397, 2015

Molecular iodine initiates hydroborations of alkenes with N-heterocyclic carbene boranes. Journal of the American Chemical Society 135(38): 14433-7, 2013