Literature DB >> 23496033

Complementary regioselectivity in Rh(III)-catalyzed insertions of potassium vinyltrifluoroborate via C-H activation: preparation and use of 4-trifluoroboratotetrahydroisoquinolones.

Marc Presset1, Daniel Oehlrich, Frederik Rombouts, Gary A Molander.   

Abstract

Potassium vinyltrifluoroborate was found to be an efficient partner with benzamide derivatives for Rh(III)-catalyzed annulations. 4-Trifluoroboratotetrahydroisoquinolones were generated under mild conditions, affording a regioisomerically complementary substitution pattern to other alkenes in related reactions. These new boron-containing building blocks were derivatized by N-arylations, retaining the boron substituent for further elaboration.

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Year:  2013        PMID： 23496033      PMCID： PMC3663910          DOI： 10.1021/ol400307d

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  49 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

2.  The atom economy--a search for synthetic efficiency.

Authors:  B M Trost
Journal:  Science       Date:  1991-12-06       Impact factor: 47.728

3.  Rhodium(III)-catalyzed intramolecular annulation through C-H activation: total synthesis of (±)-antofine, (±)-septicine, (±)-tylophorine, and rosettacin.

Authors:  Xianxiu Xu; Yu Liu; Cheol-Min Park
Journal:  Angew Chem Int Ed Engl       Date:  2012-08-21       Impact factor: 15.336

4.  Rhodium(III)-catalyzed arylation of Boc-imines via C-H bond functionalization.

Authors:  Andy S Tsai; Michael E Tauchert; Robert G Bergman; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2011-01-04       Impact factor: 15.419

5.  Oxidation of organotrifluoroborates via oxone.

Authors:  Gary A Molander; Livia N Cavalcanti
Journal:  J Org Chem       Date:  2010-12-30       Impact factor: 4.354

6.  Synthesis of pi-conjugated dendrimers based on azaborines.

Authors:  Tomohiro Agou; Tatsuo Kojima; Junji Kobayashi; Takayuki Kawashima
Journal:  Org Lett       Date:  2009-08-20       Impact factor: 6.005

7.  Access to sultams by rhodium(III)-catalyzed directed C-H activation.

Authors:  Manh V Pham; Baihua Ye; Nicolai Cramer
Journal:  Angew Chem Int Ed Engl       Date:  2012-09-23       Impact factor: 15.336

8.  Escape from flatland: increasing saturation as an approach to improving clinical success.

Authors:  Frank Lovering; Jack Bikker; Christine Humblet
Journal:  J Med Chem       Date:  2009-11-12       Impact factor: 7.446

9.  Rhodium(III)-catalyzed oxidative C-H coupling of N-methoxybenzamides with aryl boronic acids: one-pot synthesis of phenanthridinones.

Authors:  Jaganathan Karthikeyan; Radhakrishnan Haridharan; Chien-Hong Cheng
Journal:  Angew Chem Int Ed Engl       Date:  2012-10-26       Impact factor: 15.336

10.  Chiral cyclopentadienyl ligands as stereocontrolling element in asymmetric C-H functionalization.

Authors:  Baihua Ye; Nicolai Cramer
Journal:  Science       Date:  2012-10-26       Impact factor: 47.728
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  14 in total

1.  Ligand-Accelerated ortho-C-H Olefination of Phenylacetic Acids.

Authors:  Keary M Engle; Navid Dastbaravardeh; Peter S Thuy-Boun; Dong-Hui Wang; Aaron C Sather; Jin-Quan Yu
Journal:  Organic Synth       Date:  2015-03-12

2.  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

3.  Rhodium(III)-Catalyzed C-H Activation Mediated Synthesis of Isoquinolones from Amides and Cyclopropenes.

Authors:  Todd K Hyster; Tomislav Rovis
Journal:  Synlett       Date:  2013       Impact factor: 2.454

Review 4.  A Simple and Versatile Amide Directing Group for C-H Functionalizations.

Authors:  Ru-Yi Zhu; Marcus E Farmer; Yan-Qiao Chen; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2016-08-01       Impact factor: 15.336

5.  Expeditious Synthesis of Isoquinolones and Isocoumarins with a Vinyl Borane as an Acetylene Equivalent.

Authors:  Momar Toure; Saul Jaime-Figueroa; George M Burslem; Craig M Crews
Journal:  European J Org Chem       Date:  2016-07-26

6.  Pd(II)-catalyzed C-H functionalizations directed by distal weakly coordinating functional groups.

Authors:  Gang Li; Li Wan; Guofu Zhang; Dasheng Leow; Jillian Spangler; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2015-03-24       Impact factor: 15.419

7.  Synthesis of Secondary Unsaturated Lactams via an Aza-Heck Reaction.

Authors:  Scott A Shuler; Guoyin Yin; Sarah B Krause; Caroline M Vesper; Donald A Watson
Journal:  J Am Chem Soc       Date:  2016-10-18       Impact factor: 15.419

Review 8.  Applications of Palladium-Catalyzed C-N Cross-Coupling Reactions.

Authors:  Paula Ruiz-Castillo; Stephen L Buchwald
Journal:  Chem Rev       Date:  2016-09-30       Impact factor: 60.622

9.  From Pd(OAc)2 to Chiral Catalysts: The Discovery and Development of Bifunctional Mono-N-Protected Amino Acid Ligands for Diverse C-H Functionalization Reactions.

Authors:  Qian Shao; Kevin Wu; Zhe Zhuang; Shaoqun Qian; Jin-Quan Yu
Journal:  Acc Chem Res       Date:  2020-03-31       Impact factor: 22.384

Review 10.  Developing ligands for palladium(II)-catalyzed C-H functionalization: intimate dialogue between ligand and substrate.

Authors:  Keary M Engle; Jin-Quan Yu
Journal:  J Org Chem       Date:  2013-05-03       Impact factor: 4.354
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