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Literature DB >> 23607624

Enantioselective redox-relay oxidative heck arylations of acyclic alkenyl alcohols using boronic acids.

Tian-Sheng Mei¹, Erik W Werner, Alexander J Burckle, Matthew S Sigman.

Abstract

A general, highly selective asymmetric redox-relay oxidative Heck reaction using achiral or racemic acyclic alkenols and boronic acid derivatives is reported. This reaction delivers remotely functionalized arylated carbonyl products from acyclic alkenol substrates, with excellent enantioselectivity under mild conditions, bearing a range of useful functionality. A preliminary mechanistic investigation suggests that the regioselectivity of the initial migratory insertion is highly dependent on the electronic nature of the boronic acid and more subtle electronic effects of the alkenyl alcohol.

Entities: Chemical Disease Gene

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Year: 2013 PMID： 23607624 PMCID： PMC3698857 DOI： 10.1021/ja402916z

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

39 in total

1. The asymmetric intramolecular Heck reaction in natural product total synthesis.

Authors: Amy B Dounay; Larry E Overman
Journal: Chem Rev Date: 2003-08 Impact factor: 60.622

2. Redox economy in organic synthesis.

Authors: Noah Z Burns; Phil S Baran; Reinhard W Hoffmann
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

3. The asymmetric Heck and related reactions.

Authors: Dennis Mc Cartney; Patrick J Guiry
Journal: Chem Soc Rev Date: 2011-06-15 Impact factor: 54.564

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

Review 5. Use of 13C NMR chemical shift as QSAR/QSPR descriptor.

Authors: Rajeshwar P Verma; Corwin Hansch
Journal: Chem Rev Date: 2011-03-25 Impact factor: 60.622

6. A highly selective and general palladium catalyst for the oxidative Heck reaction of electronically nonbiased olefins.

Authors: Erik W Werner; Matthew S Sigman
Journal: J Am Chem Soc Date: 2010-10-13 Impact factor: 15.419

7. Oxidative palladium(II) catalysis: A highly efficient and chemoselective cross-coupling method for carbon-carbon bond formation under base-free and nitrogenous-ligand conditions.

Authors: Kyung Soo Yoo; Cheol Hwan Yoon; Rajesh K Mishra; Young Chun Jung; Sung Wook Yi; Kyung Woon Jung
Journal: J Am Chem Soc Date: 2006-12-20 Impact factor: 15.419

8. Asymmetric intermolecular heck-type reaction of acyclic alkenes via oxidative palladium(II) catalysis.

Authors: Kyung Soo Yoo; Chan Pil Park; Cheol Hwan Yoon; Satoshi Sakaguchi; Justin O'Neill; Kyung Woon Jung
Journal: Org Lett Date: 2007-08-31 Impact factor: 6.005

9. Asymmetric intermolecular boron Heck-type reactions via oxidative palladium(II) catalysis with chiral tridentate NHC-amidate-alkoxide ligands.

Authors: Kyung Soo Yoo; Justin O'Neill; Satoshi Sakaguchi; Richard Giles; Joo Ho Lee; Kyung Woon Jung
Journal: J Org Chem Date: 2010-01-01 Impact factor: 4.354

10. A general and efficient catalyst system for a Wacker-type oxidation using TBHP as the terminal oxidant: application to classically challenging substrates.

Authors: Brian W Michel; Andrew M Camelio; Candace N Cornell; Matthew S Sigman
Journal: J Am Chem Soc Date: 2009-05-06 Impact factor: 15.419

59 in total

Enantioselective redox-relay oxidative heck arylations of acyclic alkenyl alcohols using boronic acids.

1. The asymmetric intramolecular Heck reaction in natural product total synthesis.

2. Redox economy in organic synthesis.

3. The asymmetric Heck and related reactions.

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

Review 5. Use of 13C NMR chemical shift as QSAR/QSPR descriptor.

6. A highly selective and general palladium catalyst for the oxidative Heck reaction of electronically nonbiased olefins.

7. Oxidative palladium(II) catalysis: A highly efficient and chemoselective cross-coupling method for carbon-carbon bond formation under base-free and nitrogenous-ligand conditions.

8. Asymmetric intermolecular heck-type reaction of acyclic alkenes via oxidative palladium(II) catalysis.

9. Asymmetric intermolecular boron Heck-type reactions via oxidative palladium(II) catalysis with chiral tridentate NHC-amidate-alkoxide ligands.

10. A general and efficient catalyst system for a Wacker-type oxidation using TBHP as the terminal oxidant: application to classically challenging substrates.

1. Reaction design, discovery, and development as a foundation to function-oriented synthesis.

2. Merging allylic carbon-hydrogen and selective carbon-carbon bond activation.

3. Second-Generation Palladium Catalyst System for Transannular C-H Functionalization of Azabicycloalkanes.

4. Alkenyl carbonyl derivatives in enantioselective redox relay Heck reactions: accessing α,β-unsaturated systems.

5. Direct Synthesis of Secondary Benzylic Alcohols Enabled by Photoredox/Ni Dual-Catalyzed Cross-Coupling.

6. Interrogating selectivity in catalysis using molecular vibrations.

7. Palladium-Catalyzed Enantioselective Redox-Relay Heck Arylation of 1,1-Disubstituted Homoallylic Alcohols.

8. Transition State Force Field for the Asymmetric Redox-Relay Heck Reaction.

9. Palladium-Catalyzed Enantioselective Intermolecular Coupling of Phenols and Allylic Alcohols.

10. Oxidative Heck vinylation for the synthesis of complex dienes and polyenes.