Literature DB >> 28205265

Borylative Radical Cyclizations of Benzo[3,4]cyclodec-3-ene-1,5-diynes and N-Heterocyclic Carbene-Boranes.

Takashi Watanabe1, Daisuke Hirose2, Dennis P Curran3, Tsuyoshi Taniguchi1.   

Abstract

Borylative radical cyclization of benzo[3,4]cyclodec-3-ene-1,5-diynes to provide 5-borylated 6,7,8,9-tetrahydrobenzo[a]azulenes has been developed. The experimental results suggest that the reaction proceeds by a radical chain mechanism, in which di-tert-butyl hyponitrite (TBHN) works as a good radical initiator to form boryl radicals from N-heterocyclic carbene-boranes (NHC-boranes). The present reaction is a rare model that illustrates addition of boryl radicals to alkynes.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkynes; boron; main group chemistry; radical reactions; strained molecules

Year:  2017        PMID： 28205265     DOI： 10.1002/chem.201700689

Source DB:  PubMed          Journal:  Chemistry        ISSN： 0947-6539            Impact factor:   5.236


  7 in total

1.  Nucleophilic Addition of Enolates to 1,4-Dehydrobenzene Diradicals Derived from Enediynes: Synthesis of Functionalized Aromatics.

Authors:  Annadka Shrinidhi; Charles L Perrin
Journal:  ACS Omega       Date:  2022-06-23

2.  NHC induced radical formation via homolytic cleavage of B-B bonds and its role in organic reactions.

Authors:  Laura Kuehn; Ludwig Zapf; Luis Werner; Martin Stang; Sabrina Würtemberger-Pietsch; Ivo Krummenacher; Holger Braunschweig; Emmanuel Lacôte; Todd B Marder; Udo Radius
Journal:  Chem Sci       Date:  2022-06-07       Impact factor: 9.969

3.  Regioselective radical α-borylation of α,β-unsaturated carbonyl compounds for direct synthesis of α-borylcarbonyl molecules.

Authors:  Shi-Chao Ren; Feng-Lian Zhang; Ai-Qing Xu; Yinuo Yang; Min Zheng; Xiaoguo Zhou; Yao Fu; Yi-Feng Wang
Journal:  Nat Commun       Date:  2019-04-29       Impact factor: 14.919

Review 4.  New avenues for C-B bond formation via radical intermediates.

Authors:  Florian W Friese; Armido Studer
Journal:  Chem Sci       Date:  2019-09-03       Impact factor: 9.825

5.  Transition Metal-Free 1,2-Carboboration of Unactivated Alkenes.

Authors:  Ying Cheng; Christian Mück-Lichtenfeld; Armido Studer
Journal:  J Am Chem Soc       Date:  2018-05-15       Impact factor: 15.419

6.  Reductive α-borylation of α,β-unsaturated esters using NHC-BH3 activated by I2 as a metal-free route to α-boryl esters.

Authors:  James E Radcliffe; Valerio Fasano; Ralph W Adams; Peiran You; Michael J Ingleson
Journal:  Chem Sci       Date:  2018-11-19       Impact factor: 9.825

7.  Stereoselective hydrogen atom transfer to acyclic radicals: a switch enabling diastereodivergent borylative radical cascades.

Authors:  Tian Ye; Feng-Lian Zhang; Hui-Min Xia; Xi Zhou; Zhi-Xiang Yu; Yi-Feng Wang
Journal:  Nat Commun       Date:  2022-01-20       Impact factor: 17.694
  7 in total

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