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Literature DB >> 26611496

Ligand-Promoted Borylation of C(sp(3))-H Bonds with Palladium(II) Catalysts.

Jian He¹, Heng Jiang¹, Ryosuke Takise¹, Ru-Yi Zhu¹, Gang Chen¹, Hui-Xiong Dai¹, T G Murali Dhar², Jun Shi³, Hao Zhang³, Peter T W Cheng³, Jin-Quan Yu⁴.

Abstract

A quinoline-based ligand effectively promotes the palladium-catalyzed borylation of C(sp(3))-H bonds. Primary β-C(sp(3))-H bonds in carboxylic acid derivatives as well as secondary C(sp(3))-H bonds in a variety of carbocyclic rings, including cyclopropanes, cyclobutanes, cyclopentanes, cyclohexanes, and cycloheptanes, can thus be borylated. This directed borylation method complements existing iridium(I)- and rhodium(I)-catalyzed C-H borylation reactions in terms of scope and operational conditions.

Entities: Chemical Disease Species

Keywords: CH activation; amino acids; borylation; palladium; synthetic methods

Mesh：

Substances：

Year: 2015 PMID： 26611496 PMCID： PMC4821169 DOI： 10.1002/anie.201509996

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

48 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. Selective C-H borylation of alkenes by palladium pincer complex catalyzed oxidative functionalization.

Authors: Nicklas Selander; Benjamin Willy; Kálmán J Szabó
Journal: Angew Chem Int Ed Engl Date: 2010-06-01 Impact factor: 15.336

Review 3. Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners.

Authors: Ranjan Jana; Tejas P Pathak; Matthew S Sigman
Journal: Chem Rev Date: 2011-02-14 Impact factor: 60.622

4. 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

5. Stereodivergent synthesis of arylcyclopropylamines by sequential C-H borylation and Suzuki-Miyaura coupling.

Authors: Shin Miyamura; Misaho Araki; Takayoshi Suzuki; Junichiro Yamaguchi; Kenichiro Itami
Journal: Angew Chem Int Ed Engl Date: 2014-10-27 Impact factor: 15.336

6. Palladium-catalyzed, direct boronic acid synthesis from aryl chlorides: a simplified route to diverse boronate ester derivatives.

Authors: Gary A Molander; Sarah L J Trice; Spencer D Dreher
Journal: J Am Chem Soc Date: 2010-11-24 Impact factor: 15.419

7. Catalytic, Regiospecific End-Functionalization of Alkanes: Rhenium-Catalyzed Borylation under Photochemical Conditions.

Authors:
Journal: Angew Chem Int Ed Engl Date: 1999-11-15 Impact factor: 15.336

8. Synthesis of 1-borylisoindoles via palladium-catalyzed dehydrogenation/C-H borylation of isoindolines.

Authors: Toshimichi Ohmura; Akihito Kijima; Michinori Suginome
Journal: J Am Chem Soc Date: 2009-05-06 Impact factor: 15.419

9. Directed ortho borylation of functionalized arenes catalyzed by a silica-supported compact phosphine-iridium system.

Authors: Soichiro Kawamorita; Hirohisa Ohmiya; Kenji Hara; Atsushi Fukuoka; Masaya Sawamura
Journal: J Am Chem Soc Date: 2009-04-15 Impact factor: 15.419

10. Stereospecific pd-catalyzed cross-coupling reactions of secondary alkylboron nucleophiles and aryl chlorides.

Authors: Ling Li; Shibin Zhao; Amruta Joshi-Pangu; Mohamed Diane; Mark R Biscoe
Journal: J Am Chem Soc Date: 2014-09-23 Impact factor: 15.419

19 in total

1. Ligand-Enabled Arylation of γ-C-H Bonds.

Authors: Suhua Li; Ru-Yi Zhu; Kai-Jiong Xiao; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2016-02-25 Impact factor: 15.336

2. Palladium-Catalyzed Transformations of Alkyl C-H Bonds.

Authors: Jian He; Masayuki Wasa; Kelvin S L Chan; Qian Shao; Jin-Quan Yu
Journal: Chem Rev Date: 2016-12-02 Impact factor: 60.622

Review 3. Complementary Strategies for Directed C(sp³ )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.

Authors: John C K Chu; Tomislav Rovis
Journal: Angew Chem Int Ed Engl Date: 2017-12-05 Impact factor: 15.336

Ligand-Promoted Borylation of C(sp(3))-H Bonds with Palladium(II) Catalysts.

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

2. Selective C-H borylation of alkenes by palladium pincer complex catalyzed oxidative functionalization.

Review 3. Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners.

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

5. Stereodivergent synthesis of arylcyclopropylamines by sequential C-H borylation and Suzuki-Miyaura coupling.

6. Palladium-catalyzed, direct boronic acid synthesis from aryl chlorides: a simplified route to diverse boronate ester derivatives.

7. Catalytic, Regiospecific End-Functionalization of Alkanes: Rhenium-Catalyzed Borylation under Photochemical Conditions.

8. Synthesis of 1-borylisoindoles via palladium-catalyzed dehydrogenation/C-H borylation of isoindolines.

9. Directed ortho borylation of functionalized arenes catalyzed by a silica-supported compact phosphine-iridium system.

10. Stereospecific pd-catalyzed cross-coupling reactions of secondary alkylboron nucleophiles and aryl chlorides.

1. Ligand-Enabled Arylation of γ-C-H Bonds.

2. Palladium-Catalyzed Transformations of Alkyl C-H Bonds.

Review 3. Complementary Strategies for Directed C(sp³ )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.

4. Ligand-accelerated enantioselective methylene C(sp3)-H bond activation.

5. Accessing 1,2-Substituted Cyclobutanes through 1,2-Azaborine Photoisomerization.

6. Nickel-Catalyzed Reduction of Secondary and Tertiary Amides.

7. Nickel-Catalyzed Esterification of Aliphatic Amides.

8. An Epoxide-Mediated Deprotection Method for Acidic Amide Auxiliary.

9. Iridium-Catalyzed, Hydrosilyl-Directed Borylation of Unactivated Alkyl C-H Bonds.

10. Ligand-Enabled γ-C(sp(3))-H Olefination of Amines: En Route to Pyrrolidines.

Review 3. Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners.

Review 3. Complementary Strategies for Directed C(sp3 )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.

Review 3. Complementary Strategies for Directed C(sp³ )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.