Literature DB >> 34431676

The Versatile Reaction Chemistry of an Alpha-Boryl Diazo Compound.

Yao Liu1, Raimon Puig de la Bellacasa2, Bo Li1, Ana Belén Cuenca2, Shih-Yuan Liu1.   

Abstract

The first α-boryl diazo compound that is capable of engaging in classic synthetic organic diazo reaction chemistry is described. The diazomethyl-1,2-azaborine 1, which is a BN isostere of phenyldiazomethane, is significantly more stable than phenyldiazomethane; its reaction chemistry ranges from C-H activation, O-H activation, [3+2] cycloaddition, and halogenation, to Ru-catalyzed carbonyl olefination. The demonstrated broad range of reactivity of diazomethyl-1,2-azaborine 1 makes it an exceptionally versatile synthetic building block for the 1,2-azaborine heterocyclic motif.

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Year:  2021        PMID： 34431676      PMCID： PMC9165608          DOI： 10.1021/jacs.1c06112

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   16.383


  45 in total

1.  Resonance stabilization energy of 1,2-azaborines: a quantitative experimental study by reaction calorimetry.

Authors:  Patrick G Campbell; Eric R Abbey; Doinita Neiner; Daniel J Grant; David A Dixon; Shih-Yuan Liu
Journal:  J Am Chem Soc       Date:  2010-12-08       Impact factor: 15.419

2.  Late-stage functionalization of BN-heterocycles.

Authors:  Cameron R McConnell; Shih-Yuan Liu
Journal:  Chem Soc Rev       Date:  2019-07-01       Impact factor: 54.564

3.  Successive carbene insertion into 9-phenyl-9-borafluorene.

Authors:  Tyler A Bartholome; Kristen R Bluer; Caleb D Martin
Journal:  Dalton Trans       Date:  2019-05-15       Impact factor: 4.390

4.  Opportune gem-Silylborylation of Carbonyl Compounds: A Modular and Stereocontrolled Entry to Tetrasubstituted Olefins.

Authors:  Enrico La Cascia; Ana B Cuenca; Elena Fernández
Journal:  Chemistry       Date:  2016-11-11       Impact factor: 5.236

5.  Copper-catalyzed synthesis of 2,4-disubstituted allenoates from α-diazoesters.

Authors:  Matthew Hassink; Xiaozhong Liu; Joseph M Fox
Journal:  Org Lett       Date:  2011-04-12       Impact factor: 6.005

6.  1,2-Azaborine's Distinct Electronic Structure Unlocks Two New Regioisomeric Building Blocks via Resolution Chemistry.

Authors:  Cameron R McConnell; Fredrik Haeffner; Andrew W Baggett; Shih-Yuan Liu
Journal:  J Am Chem Soc       Date:  2019-05-23       Impact factor: 15.419

7.  Mild and Complete Carbonyl Ligand Scission on a Mononuclear Transition Metal Complex.

Authors:  Holger Braunschweig; Mehmet Ali Celik; Rian D Dewhurst; Stephanie Kachel; Benedikt Wennemann
Journal:  Angew Chem Int Ed Engl       Date:  2016-03-15       Impact factor: 15.336

8.  Unsymmetrical 1,1-diborated multisubstituted sp(3)-carbons formed via a metal-free concerted-asynchronous mechanism.

Authors:  Ana B Cuenca; Jessica Cid; Diego García-López; Jorge J Carbó; Elena Fernández
Journal:  Org Biomol Chem       Date:  2015-10-07       Impact factor: 3.876

9.  Synthesis of High Oxidation State Molybdenum Imido Heteroatom-Substituted Alkylidene Complexes.

Authors:  Erik M Townsend; Stefan M Kilyanek; Richard R Schrock; Peter Müller; Stacey J Smith; Amir H Hoveyda
Journal:  Organometallics       Date:  2013-08-26       Impact factor: 3.876

10.  Simple access to elusive α-boryl carbanions and their alkylation: an umpolung construction for organic synthesis.

Authors:  Kai Hong; Xun Liu; James P Morken
Journal:  J Am Chem Soc       Date:  2014-07-16       Impact factor: 15.419
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  1 in total

1.  Design and synthesis of stable four-coordinated benzotriazole-borane with tunable fluorescence emission.

Authors:  Qi Tang; Shi-Jun Li; Xiaohan Ye; Teng Yuan; Kai Zhao; Ying He; Chuan Shan; Lukasz Wojtas; David Richardson; Yu Lan; Xiaodong Shi
Journal:  Chem Sci       Date:  2022-04-18       Impact factor: 9.969
  1 in total

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