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Literature DB >> 25822198

Ligand-enabled cross-coupling of C(sp(3))-H bonds with arylsilanes.

Jian He¹, Ryosuke Takise¹, Haiyan Fu¹, Jin-Quan Yu¹.

Abstract

Pd(II)-catalyzed cross-coupling of C(sp(3))-H bonds with organosilicon coupling partners has been achieved for the first time. The use of a newly developed quinoline-based ligand is essential for the cross-coupling reactions to proceed.

Entities: Chemical Disease Species

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Year: 2015 PMID： 25822198 PMCID： PMC4432906 DOI： 10.1021/jacs.5b00890

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

42 in total

Review 1. Design and implementation of new, silicon-based, cross-coupling reactions: importance of silicon-oxygen bonds.

Authors: Scott E Denmark; Ramzi F Sweis
Journal: Acc Chem Res Date: 2002-10 Impact factor: 22.384

2. Improvements in cross coupling reactions of hypervalent siloxane derivatives.

Authors: M E Mowery; P DeShong
Journal: Org Lett Date: 1999-12-30 Impact factor: 6.005

3. Ligand-accelerated ortho-C-H alkylation of arylcarboxylic acids using alkyl boron reagents.

Authors: Peter S Thuy-Boun; Giorgio Villa; Devin Dang; Paul Richardson; Shun Su; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2013-11-08 Impact factor: 15.419

4. Pd(OAc)(2) catalyzed olefination of highly electron-deficient perfluoroarenes.

Authors: Xingang Zhang; Shilu Fan; Chun-Yang He; Xiaolong Wan; Qiao-Qiao Min; Jie Yang; Zhong-Xing Jiang
Journal: J Am Chem Soc Date: 2010-04-07 Impact factor: 15.419

5. Cross-coupling of C(sp)-H Bonds with Organometallic Reagents via Pd(II)/Pd(0) Catalysis**

Authors: Masayuki Wasa; Keary M Engle; Jin-Quan Yu
Journal: Isr J Chem Date: 2010-12 Impact factor: 3.333

6. Cross-coupling reactions of alkenylsilanolates. Investigation of the mechanism and identification of key intermediates through kinetic analysis.

Authors: Scott E Denmark; Ramzi F Sweis
Journal: J Am Chem Soc Date: 2004-04-21 Impact factor: 15.419

7. Palladium-catalyzed C-H functionalization of pyridine N-oxides: highly selective alkenylation and direct arylation with unactivated arenes.

Authors: Seung Hwan Cho; Seung Jun Hwang; Sukbok Chang
Journal: J Am Chem Soc Date: 2008-06-27 Impact factor: 15.419

8. Why does fluoride anion accelerate transmetalation between vinylsilane and palladium(II)-vinyl complex? Theoretical study.

Authors: Akihiro Sugiyama; Yu-ya Ohnishi; Mayu Nakaoka; Yoshihide Nakao; Hirofumi Sato; Shigeyoshi Sakaki; Yoshiaki Nakao; Tamejiro Hiyama
Journal: J Am Chem Soc Date: 2008-09-04 Impact factor: 15.419

9. Ligand-enabled methylene C(sp3)-H bond activation with a Pd(II) catalyst.

Authors: Masayuki Wasa; Kelvin S L Chan; Xing-Guo Zhang; Jian He; Masanori Miura; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2012-11-05 Impact factor: 15.419

10. Ligand-enabled triple C-H activation reactions: one-pot synthesis of diverse 4-aryl-2-quinolinones from propionamides.

Authors: Youqian Deng; Wei Gong; Jian He; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2014-05-14 Impact factor: 15.336

14 in total

1. 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

2. Ligand-Enabled Alkynylation of C(sp³ )-H Bonds with Palladium(II) Catalysts.

Authors: Haiyan Fu; Peng-Xiang Shen; Jian He; Fanglin Zhang; Suhua Li; Peng Wang; Tao Liu; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2017-01-12 Impact factor: 15.336

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

4. Iridium-catalysed arylation of C-H bonds enabled by oxidatively induced reductive elimination.

Authors: Kwangmin Shin; Yoonsu Park; Mu-Hyun Baik; Sukbok Chang
Journal: Nat Chem Date: 2017-12-11 Impact factor: 24.427

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

Authors: Bin Liu; Andrew M Romine; Camille Z Rubel; Keary M Engle; Bing-Feng Shi
Journal: Chem Rev Date: 2021-10-29 Impact factor: 60.622

6. Palladium-Catalyzed Enantioselective β-C(sp³)-H Activation Reactions of Aliphatic Acids: A Retrosynthetic Surrogate for Enolate Alkylation and Conjugate Addition.

Authors: Erika L Lucas; Nelson Y S Lam; Zhe Zhuang; Hau Sun Sam Chan; Daniel A Strassfeld; Jin-Quan Yu
Journal: Acc Chem Res Date: 2022-01-25 Impact factor: 24.466

Ligand-enabled cross-coupling of C(sp(3))-H bonds with arylsilanes.

Review 1. Design and implementation of new, silicon-based, cross-coupling reactions: importance of silicon-oxygen bonds.

2. Improvements in cross coupling reactions of hypervalent siloxane derivatives.

3. Ligand-accelerated ortho-C-H alkylation of arylcarboxylic acids using alkyl boron reagents.

4. Pd(OAc)(2) catalyzed olefination of highly electron-deficient perfluoroarenes.

5. Cross-coupling of C(sp)-H Bonds with Organometallic Reagents via Pd(II)/Pd(0) Catalysis**

6. Cross-coupling reactions of alkenylsilanolates. Investigation of the mechanism and identification of key intermediates through kinetic analysis.

7. Palladium-catalyzed C-H functionalization of pyridine N-oxides: highly selective alkenylation and direct arylation with unactivated arenes.

8. Why does fluoride anion accelerate transmetalation between vinylsilane and palladium(II)-vinyl complex? Theoretical study.

9. Ligand-enabled methylene C(sp3)-H bond activation with a Pd(II) catalyst.

10. Ligand-enabled triple C-H activation reactions: one-pot synthesis of diverse 4-aryl-2-quinolinones from propionamides.

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

2. Ligand-Enabled Alkynylation of C(sp³ )-H Bonds with Palladium(II) Catalysts.

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. Iridium-catalysed arylation of C-H bonds enabled by oxidatively induced reductive elimination.

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

6. Palladium-Catalyzed Enantioselective β-C(sp³)-H Activation Reactions of Aliphatic Acids: A Retrosynthetic Surrogate for Enolate Alkylation and Conjugate Addition.

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

8. Ligand-Promoted C(sp(3) )-H Olefination en Route to Multi-functionalized Pyrazoles.

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

10. Coordinating activation strategy for C(sp(3))-H/C(sp(3))-H cross-coupling to access β-aromatic α-amino acids.

Review 1. Design and implementation of new, silicon-based, cross-coupling reactions: importance of silicon-oxygen 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.

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

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