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Literature DB >> 20852803

Electronic effects in iridium C-H borylations: insights from unencumbered substrates and variation of boryl ligand substituents.

Britt A Vanchura¹, Sean M Preshlock, Philipp C Roosen, Venkata A Kallepalli, Richard J Staples, Robert E Maleczka, Daniel A Singleton, Milton R Smith.

Abstract

Experiment and theory favour a model of C-H borylation where significant proton transfer character exists in the transition state.

Entities: Chemical Disease Species

Mesh：

Substances：

Year: 2010 PMID： 20852803 PMCID： PMC3573526 DOI： 10.1039/c0cc02041a

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

14 in total

1. Trans influence of boryl ligands and comparison with C, SI, and SN ligands.

Authors: Jun Zhu; Zhenyang Lin; Todd B Marder
Journal: Inorg Chem Date: 2005-12-12 Impact factor: 5.165

2. Parameters for the Description of Transition States.

Authors: J E Leffler
Journal: Science Date: 1953-03-27 Impact factor: 47.728

3. Boryl ligands and their roles in metal-catalysed borylation reactions.

Authors: Li Dang; Zhenyang Lin; Todd B Marder
Journal: Chem Commun (Camb) Date: 2009-05-18 Impact factor: 6.222

4. C-H activation for the construction of C-B bonds.

Authors: Ibraheem A I Mkhalid; Jonathan H Barnard; Todd B Marder; Jaclyn M Murphy; John F Hartwig
Journal: Chem Rev Date: 2010-02-10 Impact factor: 60.622

5. Origins of the selectivity for borylation of primary over secondary C-H bonds catalyzed by Cp*-rhodium complexes.

Authors: Carolyn S Wei; Carlos A Jiménez-Hoyos; Marcelo F Videa; John F Hartwig; Michael B Hall
Journal: J Am Chem Soc Date: 2010-03-10 Impact factor: 15.419

6. Experimental and computational evidence for a boron-assisted, sigma-bond metathesis pathway for alkane borylation.

Authors: Charles Edwin Webster; Yubo Fan; Michael B Hall; Doris Kunz; John F Hartwig
Journal: J Am Chem Soc Date: 2003-01-29 Impact factor: 15.419

7. Iridium-catalyzed borylation of benzene with diboron. Theoretical elucidation of catalytic cycle including unusual iridium(v) intermediate.

Authors: Hitoshi Tamura; Hideki Yamazaki; Hirofumi Sato; Shigeyoshi Sakaki
Journal: J Am Chem Soc Date: 2003-12-24 Impact factor: 15.419

8. Time-resolved IR studies on the mechanism for the functionalization of primary C-H bonds by photoactivated Cp*W(CO)3(Bpin).

Authors: Karma R Sawyer; James F Cahoon; Jennifer E Shanoski; Elizabeth A Glascoe; Matthias F Kling; Jacob P Schlegel; Matthew C Zoerb; Marko Hapke; John F Hartwig; Charles Edwin Webster; Charles B Harris
Journal: J Am Chem Soc Date: 2010-02-17 Impact factor: 15.419

9. Pronounced effects of substituents on the iridium-catalyzed borylation of aryl C-H bonds.

Authors: Carl W Liskey; Carolyn S Wei; Dale R Pahls; John F Hartwig
Journal: Chem Commun (Camb) Date: 2009-08-20 Impact factor: 6.222

10. Transition-state charge transfer reveals electrophilic, ambiphilic, and nucleophilic carbon-hydrogen bond activation.

Authors: Daniel H Ess; Robert J Nielsen; William A Goddard; Roy A Periana
Journal: J Am Chem Soc Date: 2009-08-26 Impact factor: 15.419

21 in total

1. Arylphosphonate-Directed Ortho C-H Borylation: Rapid Entry into Highly-Substituted Phosphoarenes.

Authors: Feiyang Xu; Olivia M Duke; Daniel Rojas; Hanka M Eichelberger; Raphael S Kim; Timothy B Clark; Donald A Watson
Journal: J Am Chem Soc Date: 2020-07-02 Impact factor: 15.419

2. C-H arylation of pyridines: high regioselectivity as a consequence of the electronic character of C-H bonds and heteroarene ring.

Authors: Pengfei Guo; Jung Min Joo; Souvik Rakshit; Dalibor Sames
Journal: J Am Chem Soc Date: 2011-09-22 Impact factor: 15.419

3. Reversible Borylene Formation from Ring Opening of Pinacolborane and Other Intermediates Generated from Five-Coordinate Tris-Boryl Complexes: Implications for Catalytic C-H Borylation.

Authors: Behnaz Ghaffari; Britt A Vanchura; Ghayoor A Chotana; Richard J Staples; Daniel Holmes; Robert E Maleczka; Milton R Smith
Journal: Organometallics Date: 2015-08-11 Impact factor: 3.876

Electronic effects in iridium C-H borylations: insights from unencumbered substrates and variation of boryl ligand substituents.

1. Trans influence of boryl ligands and comparison with C, SI, and SN ligands.

2. Parameters for the Description of Transition States.

3. Boryl ligands and their roles in metal-catalysed borylation reactions.

4. C-H activation for the construction of C-B bonds.

5. Origins of the selectivity for borylation of primary over secondary C-H bonds catalyzed by Cp*-rhodium complexes.

6. Experimental and computational evidence for a boron-assisted, sigma-bond metathesis pathway for alkane borylation.

7. Iridium-catalyzed borylation of benzene with diboron. Theoretical elucidation of catalytic cycle including unusual iridium(v) intermediate.

8. Time-resolved IR studies on the mechanism for the functionalization of primary C-H bonds by photoactivated Cp*W(CO)3(Bpin).

9. Pronounced effects of substituents on the iridium-catalyzed borylation of aryl C-H bonds.

10. Transition-state charge transfer reveals electrophilic, ambiphilic, and nucleophilic carbon-hydrogen bond activation.

1. Arylphosphonate-Directed Ortho C-H Borylation: Rapid Entry into Highly-Substituted Phosphoarenes.

2. C-H arylation of pyridines: high regioselectivity as a consequence of the electronic character of C-H bonds and heteroarene ring.

3. Reversible Borylene Formation from Ring Opening of Pinacolborane and Other Intermediates Generated from Five-Coordinate Tris-Boryl Complexes: Implications for Catalytic C-H Borylation.

4. Cobalt Pincer Complexes in Catalytic C-H Borylation: The Pincer Ligand Flips Rather Than Dearomatizes.

5. Practical One-Pot C-H Activation/Borylation/Oxidation: Preparation of 3-Bromo-5-methylphenol on a Multigram Scale.

6. Outer-sphere direction in iridium C-H borylation.

7. Catalytic borylation of methane.

8. N-Directed aliphatic C-H borylation using borenium cation equivalents.

9. Bismuth Acetate as a Catalyst for the Sequential Protodeboronation of Di- and Triborylated Indoles.

10. Evolution of C-H Bond Functionalization from Methane to Methodology.