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Literature DB >> 22703452

Outer-sphere direction in iridium C-H borylation.

Philipp C Roosen¹, Venkata A Kallepalli, Buddhadeb Chattopadhyay, Daniel A Singleton, Robert E Maleczka, Milton R Smith.

Abstract

The NHBoc group affords ortho selective C-H borylations in arenes and alkenes. Experimental and computational studies support an outer sphere mechanism where the N-H proton hydrogen bonds to a boryl ligand oxygen. The regioselectivities are unique and complement those of directed ortho metalations.

Entities: Chemical Disease

Mesh：

Substances：
Boron Compounds
Iridium

Year: 2012 PMID： 22703452 PMCID： PMC3587652 DOI： 10.1021/ja303443m

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

33 in total

1. Pd-catalyzed oxidative ortho-C-H borylation of arenes.

Authors: Hui-Xiong Dai; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2011-12-19 Impact factor: 15.419

2. A stoichiometric aromatic CbondH borylation catalyzed by iridium(i)/2,2'-bipyridine complexes at room temperature.

Authors: Tatsuo Ishiyama; Jun Takagi; John F Hartwig; Norio Miyaura
Journal: Angew Chem Int Ed Engl Date: 2002-08-16 Impact factor: 15.336

3. Remarkably selective iridium catalysts for the elaboration of aromatic C-H bonds.

Authors: Jian-Yang Cho; Man Kin Tse; Daniel Holmes; Robert E Maleczka; Milton R Smith
Journal: Science Date: 2001-11-22 Impact factor: 47.728

4. Mechanistic aspects of transition metal-catalyzed hydrogen transfer reactions.

Authors: Joseph S M Samec; Jan-E Bäckvall; Pher G Andersson; Peter Brandt
Journal: Chem Soc Rev Date: 2006-01-23 Impact factor: 54.564

5. Hydrogen bond directed highly regioselective palladium-catalyzed allylic substitution.

Authors: Gregory R Cook; Hui Yu; S Sankaranarayanan; P Sathya Shanker
Journal: J Am Chem Soc Date: 2003-04-30 Impact factor: 15.419

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

Authors: Britt A Vanchura; Sean M Preshlock; Philipp C Roosen; Venkata A Kallepalli; Richard J Staples; Robert E Maleczka; Daniel A Singleton; Milton R Smith
Journal: Chem Commun (Camb) Date: 2010-09-20 Impact factor: 6.222

7. Efficient synthesis of diborylalkenes from alkenes and diboron by a new PSiP-pincer palladium-catalyzed dehydrogenative borylation.

Authors: Jun Takaya; Naohiro Kirai; Nobuharu Iwasawa
Journal: J Am Chem Soc Date: 2011-08-02 Impact factor: 15.419

8. How the binding of substrates to a chiral polyborate counterion governs diastereoselection in an aziridination reaction: H-bonds in equipoise.

Authors: Mathew J Vetticatt; Aman A Desai; William D Wulff
Journal: J Am Chem Soc Date: 2010-09-29 Impact factor: 15.419

9. 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

10. Boc groups as protectors and directors for Ir-catalyzed C-H borylation of heterocycles.

Authors: Venkata A Kallepalli; Feng Shi; Sulagna Paul; Edith N Onyeozili; Robert E Maleczka; Milton R Smith
Journal: J Org Chem Date: 2009-12-04 Impact factor: 4.354

25 in total

1. Enantioselective Borylation of Aromatic C-H Bonds with Chiral Dinitrogen Ligands.

Authors: Bo Su; Tai-Gang Zhou; Pei-Lin Xu; Zhang-Jie Shi; John F Hartwig
Journal: Angew Chem Int Ed Engl Date: 2017-05-16 Impact factor: 15.336

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

Authors: Haixia Li; Jennifer V Obligacion; Paul J Chirik; Michael B Hall
Journal: ACS Catal Date: 2018-10-17 Impact factor: 13.084

3. Cobalt-Catalyzed Borylation of Fluorinated Arenes: Thermodynamic Control of C(sp²)-H Oxidative Addition Results in ortho-to-Fluorine Selectivity.

Authors: Tyler P Pabst; Jennifer V Obligacion; Étienne Rochette; Iraklis Pappas; Paul J Chirik
Journal: J Am Chem Soc Date: 2019-09-16 Impact factor: 15.419

4. Ir-Catalyzed ortho-Borylation of Phenols Directed by Substrate-Ligand Electrostatic Interactions: A Combined Experimental/in Silico Strategy for Optimizing Weak Interactions.

Authors: Buddhadeb Chattopadhyay; Jonathan E Dannatt; Ivonne L Andujar-De Sanctis; Kristin A Gore; Robert E Maleczka; Daniel A Singleton; Milton R Smith
Journal: J Am Chem Soc Date: 2017-05-31 Impact factor: 15.419