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Literature DB >> 22449256

Ruthenium(0)-catalyzed sp3 C-H bond arylation of benzylic amines using arylboronates.

Navid Dastbaravardeh¹, Michael Schnürch, Marko D Mihovilovic.

Abstract

A Ru-catalyzed direct arylation of benzylic sp(3) carbons of acyclic amines with arylboronates is reported. This highly regioselective and efficient transformation can be performed with various combinations of N-(2-pyridyl) substituted benzylamines and arylboronates. Substitution of the pyridine directing group in the 3-position proved to be crucial in order to achieve high arylation yields. Furthermore, the pyridine directing group can be removed in high yields via a two-step protocol.

Entities: Chemical

Year: 2012 PMID： 22449256 DOI： 10.1021/ol300627p

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

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Cited

18 in total

1. Synthesis of diarylmethylamines via palladium-catalyzed regioselective arylation of 1,1,3-triaryl-2-azaallyl anions.

Authors: Minyan Li; Baris Yücel; Javier Adrio; Ana Bellomo; Patrick J Walsh
Journal: Chem Sci Date: 2014-06-01 Impact factor: 9.825

2. Practical Alkoxythiocarbonyl Auxiliaries for Iridium(I)-Catalyzed C-H Alkylation of Azacycles.

Authors: Anh T Tran; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2017-07-24 Impact factor: 15.336

3. Intermolecular [3+2] Annulation of Cyclopropylanilines with Alkynes, Enynes, and Diynes via Visible Light Photocatalysis.

Authors: Theresa H Nguyen; Scott A Morris; Nan Zheng
Journal: Adv Synth Catal Date: 2014-09-15 Impact factor: 5.837

10. Mechanistic investigations and substrate scope evaluation of ruthenium-catalyzed direct sp3 arylation of benzylic positions directed by 3-substituted pyridines.

Authors: Navid Dastbaravardeh; Karl Kirchner; Michael Schnürch; Marko D Mihovilovic
Journal: J Org Chem Date: 2013-01-03 Impact factor: 4.354

Ruthenium(0)-catalyzed sp3 C-H bond arylation of benzylic amines using arylboronates.

1. Synthesis of diarylmethylamines via palladium-catalyzed regioselective arylation of 1,1,3-triaryl-2-azaallyl anions.

2. Practical Alkoxythiocarbonyl Auxiliaries for Iridium(I)-Catalyzed C-H Alkylation of Azacycles.

3. Intermolecular [3+2] Annulation of Cyclopropylanilines with Alkynes, Enynes, and Diynes via Visible Light Photocatalysis.

4. Ligand-Promoted meta-C-H Functionalization of Benzylamines.

Review 5. Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp³)-H Bonds.

6. Redox-neutral α-arylation of amines.

7. Iridium(I)-Catalyzed α-C(sp³)-H Alkylation of Saturated Azacycles.

8. Palladium-Catalyzed Benzylic C-H Arylation of Azaarylmethylamines.

9. α-Arylation of Saturated Azacycles and N-Methylamines via Palladium(II)-Catalyzed C(sp(3))-H Coupling.

10. Mechanistic investigations and substrate scope evaluation of ruthenium-catalyzed direct sp3 arylation of benzylic positions directed by 3-substituted pyridines.

Review 5. Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp3)-H Bonds.

Review 5. Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp³)-H Bonds.