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Literature DB >> 29697174

Copper-Catalyzed Heteroarylboration of 1,3-Dienes with 3-Bromopyridines: A cine Substitution.

Kevin B Smith¹, Yuan Huang¹, M Kevin Brown¹.

Abstract

A method for the heteroarylboration of 1,3-dienes is presented. The process involves an unusual cine substitution of 3-bromopyridine derivatives to deliver highly functionalized heterocyclic products. Mechanistic studies are included that clarify the details of this unusual process.

Entities: Chemical Disease Species

Keywords: boron; copper; dienes; heterocycles; synthetic methods

Mesh：

Substances：

Year: 2018 PMID： 29697174 PMCID： PMC6132256 DOI： 10.1002/anie.201801139

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

31 in total

1. Enantioselective construction of quaternary stereocenter through a Reissert-type reaction catalyzed by an electronically tuned bifunctional catalyst: efficient synthesis of various biologically significant compounds.

Authors: K Funabashi; H Ratni; M Kanai; M Shibasaki
Journal: J Am Chem Soc Date: 2001-10-31 Impact factor: 15.419

2. Copper/palladium synergistic catalysis for the syn- and anti-selective carboboration of alkenes.

Authors: Kaitlyn M Logan; Kevin B Smith; M Kevin Brown
Journal: Angew Chem Int Ed Engl Date: 2015-02-27 Impact factor: 15.336

3. Modular monodentate oxaphospholane ligands: utility in highly efficient and enantioselective 1,4-diboration of 1,3-dienes.

Authors: Christopher H Schuster; Bo Li; James P Morken
Journal: Angew Chem Int Ed Engl Date: 2011-07-12 Impact factor: 15.336

4. Nickel-Catalyzed Stereoselective Arylboration of Unactivated Alkenes.

Authors: Kaitlyn M Logan; Stephen R Sardini; Sean D White; M Kevin Brown
Journal: J Am Chem Soc Date: 2017-12-22 Impact factor: 15.419

5. Switchable selectivity in an NHC-catalysed dearomatizing annulation reaction.

Authors: Chang Guo; Mirco Fleige; Daniel Janssen-Müller; Constantin G Daniliuc; Frank Glorius
Journal: Nat Chem Date: 2015-08-31 Impact factor: 24.427

6. Catalytic Enantioselective Arylboration of Alkenylarenes.

Authors: Kaitlyn M Logan; M Kevin Brown
Journal: Angew Chem Int Ed Engl Date: 2016-12-21 Impact factor: 15.336

7. Enantioselective 1,2-Difunctionalization of Dienes Enabled by Chiral Palladium Complex-Catalyzed Cascade Arylation/Allylic Alkylation Reaction.

Authors: Xiang Wu; Hua-Chen Lin; Ming-Li Li; Lu-Lu Li; Zhi-Yong Han; Liu-Zhu Gong
Journal: J Am Chem Soc Date: 2015-10-15 Impact factor: 15.419

8. Pd-Catalyzed Regioselective Arylboration of Vinylarenes.

Authors: Kai Yang; Qiuling Song
Journal: Org Lett Date: 2016-10-27 Impact factor: 6.005

9. Enantioselective Aminomethylamination of Conjugated Dienes with Aminals Enabled by Chiral Palladium Complex-Catalyzed C-N Bond Activation.

Authors: Yang Liu; Yinjun Xie; Hongli Wang; Hanmin Huang
Journal: J Am Chem Soc Date: 2016-03-24 Impact factor: 15.419

10. Highly selective copper-catalyzed hydroboration of allenes and 1,3-dienes.

Authors: Kazuhiko Semba; Masataka Shinomiya; Tetsuaki Fujihara; Jun Terao; Yasushi Tsuji
Journal: Chemistry Date: 2013-04-09 Impact factor: 5.236

11 in total

1. Transition-Metal-Catalyzed 1,2-Carboboration of Alkenes: Strategies, Mechanisms, and Stereocontrol.

Authors: Zhen Liu; Yang Gao; Tian Zeng; Keary M Engle
Journal: Isr J Chem Date: 2019-09-10 Impact factor: 3.333

2. Evidence for Simultaneous Dearomatization of Two Aromatic Rings under Mild Conditions in Cu(I)-Catalyzed Direct Asymmetric Dearomatization of Pyridine.

Authors: Michael W Gribble; Richard Y Liu; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2020-06-11 Impact factor: 15.419

3. Pyridine(diimine) Iron Diene Complexes Relevant to Catalytic [2+2]-Cycloaddition Reactions.

Authors: C Rose Kennedy; Hongyu Zhong; Matthew V Joannou; Paul J Chirik
Journal: Adv Synth Catal Date: 2019-11-19 Impact factor: 5.837

4. Organoboron chemistry comes to light: recent advances in photoinduced synthetic approaches to organoboron compounds.

Authors: Viet D Nguyen; Vu T Nguyen; Shengfei Jin; Hang T Dang; Oleg V Larionov
Journal: Tetrahedron Date: 2018-12-24 Impact factor: 2.457

5. A Dual CuH- and Pd-Catalyzed Stereoselective Synthesis of Highly Substituted 1,3-Dienes.

Authors: Chuan-Jin Hou; Alexander W Schuppe; James Levi Knippel; Anton Z Ni; Stephen L Buchwald
Journal: Org Lett Date: 2021-11-02 Impact factor: 6.072

Review 6. Recent advances in Cu-catalyzed C(sp³)-Si and C(sp³)-B bond formation.

Authors: Balaram S Takale; Ruchita R Thakore; Elham Etemadi-Davan; Bruce H Lipshutz
Journal: Beilstein J Org Chem Date: 2020-04-15 Impact factor: 2.883

7. Ligand-controlled diastereodivergent, enantio- and regioselective copper-catalyzed hydroxyalkylboration of 1,3-dienes with ketones.

Authors: Jian-Jun Feng; Yan Xu; Martin Oestreich
Journal: Chem Sci Date: 2019-08-20 Impact factor: 9.825

Copper-Catalyzed Heteroarylboration of 1,3-Dienes with 3-Bromopyridines: A cine Substitution.

1. Enantioselective construction of quaternary stereocenter through a Reissert-type reaction catalyzed by an electronically tuned bifunctional catalyst: efficient synthesis of various biologically significant compounds.

2. Copper/palladium synergistic catalysis for the syn- and anti-selective carboboration of alkenes.

3. Modular monodentate oxaphospholane ligands: utility in highly efficient and enantioselective 1,4-diboration of 1,3-dienes.

4. Nickel-Catalyzed Stereoselective Arylboration of Unactivated Alkenes.

5. Switchable selectivity in an NHC-catalysed dearomatizing annulation reaction.

6. Catalytic Enantioselective Arylboration of Alkenylarenes.

7. Enantioselective 1,2-Difunctionalization of Dienes Enabled by Chiral Palladium Complex-Catalyzed Cascade Arylation/Allylic Alkylation Reaction.

8. Pd-Catalyzed Regioselective Arylboration of Vinylarenes.

9. Enantioselective Aminomethylamination of Conjugated Dienes with Aminals Enabled by Chiral Palladium Complex-Catalyzed C-N Bond Activation.

10. Highly selective copper-catalyzed hydroboration of allenes and 1,3-dienes.

1. Transition-Metal-Catalyzed 1,2-Carboboration of Alkenes: Strategies, Mechanisms, and Stereocontrol.

2. Evidence for Simultaneous Dearomatization of Two Aromatic Rings under Mild Conditions in Cu(I)-Catalyzed Direct Asymmetric Dearomatization of Pyridine.

3. Pyridine(diimine) Iron Diene Complexes Relevant to Catalytic [2+2]-Cycloaddition Reactions.

4. Organoboron chemistry comes to light: recent advances in photoinduced synthetic approaches to organoboron compounds.

5. A Dual CuH- and Pd-Catalyzed Stereoselective Synthesis of Highly Substituted 1,3-Dienes.

Review 6. Recent advances in Cu-catalyzed C(sp³)-Si and C(sp³)-B bond formation.

7. Ligand-controlled diastereodivergent, enantio- and regioselective copper-catalyzed hydroxyalkylboration of 1,3-dienes with ketones.

8. Mechanism-Based Design of an Amide-Directed Ni-Catalyzed Arylboration of Cyclopentene Derivatives.

9. Base-catalyzed aryl halide isomerization enables the 4-selective substitution of 3-bromopyridines.

Review 10. Copper-Catalyzed Borylative Couplings with C-N Electrophiles.

Review 6. Recent advances in Cu-catalyzed C(sp3)-Si and C(sp3)-B bond formation.

Review 10. Copper-Catalyzed Borylative Couplings with C-N Electrophiles.

Review 6. Recent advances in Cu-catalyzed C(sp³)-Si and C(sp³)-B bond formation.