Literature DB >> 26358769

Rhodium(III)-Catalyzed Allylic C(sp(3))-H Activation of Alkenyl Sulfonamides: Unexpected Formation of Azabicycles.

Alexis Archambeau1, Tomislav Rovis2.   

Abstract

Unsaturated N-sulfonamides undergo a Rh(III)-catalyzed allylic C(sp(3))-H activation followed by insertion with an exogenous internal alkyne. The reaction generates [3.3.0], [4.3.0], and [5.3.0] azabicyclic structures with excellent diastereoselectivity. Deuterium labeling experiments implicate a 1,3-Rh shift as a key step in the mechanism.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  1,3-migration; 4π-electrocyclization; CH insertion; azabicycles; rhodium

Mesh：

Substances：

Year:  2015        PMID： 26358769      PMCID： PMC4676418          DOI： 10.1002/anie.201504150

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  39 in total

1.  Oxidative coupling of aromatic substrates with alkynes and alkenes under rhodium catalysis.

Authors:  Tetsuya Satoh; Masahiro Miura
Journal:  Chemistry       Date:  2010-10-04       Impact factor: 5.236

Review 2.  Towards mild metal-catalyzed C-H bond activation.

Authors:  Joanna Wencel-Delord; Thomas Dröge; Fan Liu; Frank Glorius
Journal:  Chem Soc Rev       Date:  2011-06-10       Impact factor: 54.564

3.  Ruthenium(II)-catalyzed C-H bond activation and functionalization.

Authors:  Percia Beatrice Arockiam; Christian Bruneau; Pierre H Dixneuf
Journal:  Chem Rev       Date:  2012-08-31       Impact factor: 60.622

4.  Beyond directing groups: transition-metal-catalyzed C-H activation of simple arenes.

Authors:  Nadine Kuhl; Matthew N Hopkinson; Joanna Wencel-Delord; Frank Glorius
Journal:  Angew Chem Int Ed Engl       Date:  2012-09-20       Impact factor: 15.336

5.  Pyrrole synthesis via allylic sp3 C-H activation of enamines followed by intermolecular coupling with unactivated alkynes.

Authors:  Souvik Rakshit; Frederic W Patureau; Frank Glorius
Journal:  J Am Chem Soc       Date:  2010-07-21       Impact factor: 15.419

6.  Ru(II)-catalyzed intermolecular ortho-C-H amidation of aromatic ketones with sulfonyl azides.

Authors:  M Bhanuchandra; M Ramu Yadav; Raja K Rit; Malleswara Rao Kuram; Akhila K Sahoo
Journal:  Chem Commun (Camb)       Date:  2013-06-07       Impact factor: 6.222

7.  Rh(III)-catalyzed halogenation of vinylic C-H Bonds: rapid and general access to Z-halo acrylamides.

Authors:  Nadine Kuhl; Nils Schröder; Frank Glorius
Journal:  Org Lett       Date:  2013-07-25       Impact factor: 6.005

8.  C-H bond functionalization in complex organic synthesis.

Authors:  Kamil Godula; Dalibor Sames
Journal:  Science       Date:  2006-04-07       Impact factor: 47.728

9.  Rhodium(III)-catalyzed intermolecular amidation with azides via C(sp³)-H functionalization.

Authors:  Nuancheng Wang; Renhe Li; Liubo Li; Shansheng Xu; Haibin Song; Baiquan Wang
Journal:  J Org Chem       Date:  2014-05-14       Impact factor: 4.354

Review 10.  Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions: versatility and practicality.

Authors:  Xiao Chen; Keary M Engle; Dong-Hui Wang; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336
View more
  10 in total

1.  Correlating Reactivity and Selectivity to Cyclopentadienyl Ligand Properties in Rh(III)-Catalyzed C-H Activation Reactions: An Experimental and Computational Study.

Authors:  Tiffany Piou; Fedor Romanov-Michailidis; Maria Romanova-Michaelides; Kelvin E Jackson; Natthawat Semakul; Trevor D Taggart; Brian S Newell; Christopher D Rithner; Robert S Paton; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2017-01-06       Impact factor: 15.419

2.  Amide-directed photoredox-catalysed C-C bond formation at unactivated sp3 C-H bonds.

Authors:  John C K Chu; Tomislav Rovis
Journal:  Nature       Date:  2016-10-12       Impact factor: 49.962

3.  Ir-Catalyzed Intermolecular Branch-Selective Allylic C-H Amidation of Unactivated Terminal Olefins.

Authors:  Honghui Lei; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2019-02-04       Impact factor: 15.419

Review 4.  Electronic and Steric Tuning of a Prototypical Piano Stool Complex: Rh(III) Catalysis for C-H Functionalization.

Authors:  Tiffany Piou; Tomislav Rovis
Journal:  Acc Chem Res       Date:  2017-12-22       Impact factor: 22.384

5.  Regiodivergent Iridium(III)-Catalyzed Diamination of Alkenyl Amides with Secondary Amines: Complementary Access to γ- or δ-Lactams.

Authors:  John H Conway; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2017-12-26       Impact factor: 15.419

6.  Alkylation of Sulfonamides with Trichloroacetimidates under Thermal Conditions.

Authors:  Daniel R Wallach; John D Chisholm
Journal:  J Org Chem       Date:  2016-08-10       Impact factor: 4.354

Review 7.  Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.

Authors:  Philip R D Murray; James H Cox; Nicholas D Chiappini; Casey B Roos; Elizabeth A McLoughlin; Benjamin G Hejna; Suong T Nguyen; Hunter H Ripberger; Jacob M Ganley; Elaine Tsui; Nick Y Shin; Brian Koronkiewicz; Guanqi Qiu; Robert R Knowles
Journal:  Chem Rev       Date:  2021-11-23       Impact factor: 60.622

8.  Computational insights into Ir(iii)-catalyzed allylic C-H amination of terminal alkenes: mechanism, regioselectivity, and catalytic activity.

Authors:  Deng Pan; Gen Luo; Yang Yu; Jimin Yang; Yi Luo
Journal:  RSC Adv       Date:  2021-05-26       Impact factor: 4.036

9.  Convergent Synthesis of Diverse Nitrogen Heterocycles via Rh(III)-Catalyzed C-H Conjugate Addition/Cyclization Reactions.

Authors:  Adam B Weinstein; Jonathan A Ellman
Journal:  Org Lett       Date:  2016-06-23       Impact factor: 6.005

10.  Nickel(0)-catalyzed linear-selective hydroarylation of unactivated alkenes and styrenes with aryl boronic acids.

Authors:  Honggui Lv; Li-Jun Xiao; Dongbing Zhao; Qi-Lin Zhou
Journal:  Chem Sci       Date:  2018-07-18       Impact factor: 9.825
  10 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.