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Literature DB >> 28960083

A Bench-Stable, Single-Component Precatalyst for Silyl-Heck Reactions.

Sarah B Krause¹, Jesse R McAtee¹, Glenn P A Yap¹, Donald A Watson¹.

Abstract

Studies of the silyl-Heck reaction aimed at identifying active palladium complexes have revealed a new species that is formed in situ. This complex has been identified as the palladium iodide dimer, [(JessePhos)PdI2]2, which has been found to be a competent single-component precatalyst for the silyl-Heck reaction. This complex is easily prepared and is temperature, moisture, and air stable. Additionally, this precatalyst provides higher activity and greater reproducibility compared to previous systems.

Entities: Chemical Gene

Mesh：

Substances：
Palladium

Year: 2017 PMID： 28960083 PMCID： PMC5983356 DOI： 10.1021/acs.orglett.7b02807

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

16 in total

1. Stereochemical Control in Organic Synthesis Using Silicon-Containing Compounds.

Authors: Ian Fleming; Asuncion Barbero; David Walter
Journal: Chem Rev Date: 1997-10-01 Impact factor: 60.622

2. Silicon-based cross-coupling reaction: an environmentally benign version.

Authors: Yoshiaki Nakao; Tamejiro Hiyama
Journal: Chem Soc Rev Date: 2011-07-14 Impact factor: 54.564

3. Direct Synthesis of Alkenyl Boronic Esters from Unfunctionalized Alkenes: A Boryl-Heck Reaction.

Authors: William B Reid; Jesse J Spillane; Sarah B Krause; Donald A Watson
Journal: J Am Chem Soc Date: 2016-04-22 Impact factor: 15.419

4. Simplified Preparation of Trialkylvinylsilanes via the Silyl-Heck Reaction Utilizing a Second Generation Catalyst.

Authors: Jesse R McAtee; Sarah B Krause; Donald A Watson
Journal: Adv Synth Catal Date: 2015-07-14 Impact factor: 5.837

5. Sequential cross-coupling of 1,4-bissilylbutadienes: synthesis of unsymmetrical 1,4-disubstituted 1,3-butadienes.

Authors: Scott E Denmark; Steven A Tymonko
Journal: J Am Chem Soc Date: 2005-06-08 Impact factor: 15.419

6. Ruthenium-catalyzed vinylsilane synthesis and cross-coupling as a selective approach to alkenes: benzyldimethylsilyl as a robust vinylmetal functionality.

Authors: Barry M Trost; Michelle R Machacek; Zachary T Ball
Journal: Org Lett Date: 2003-05-29 Impact factor: 6.005

7. Preparation of vinyl silyl ethers and disiloxanes via the silyl-Heck reaction of silyl ditriflates.

Authors: Sara E S Martin; Donald A Watson
Journal: J Am Chem Soc Date: 2013-08-28 Impact factor: 15.419

8. The First Example of Nickel-Catalyzed Silyl-Heck Reactions: Direct Activation of Silyl Triflates Without Iodide Additives.

Authors: Jesse R McAtee; Sara E S Martin; Andrew P Cinderella; William B Reid; Keywan A Johnson; Donald A Watson
Journal: Tetrahedron Date: 2014-07-08 Impact factor: 2.457

9. Silyl-Heck Reactions for the Preparation of Unsaturated Organosilanes.

Authors: Sara E S Martin; Donald A Watson
Journal: Synlett Date: 2013-09-30 Impact factor: 2.454

10. Palladium-Catalyzed Cross-Coupling of Silyl Electrophiles with Alkylzinc Halides: A Silyl-Negishi Reaction.

Authors: Andrew P Cinderella; Bojan Vulovic; Donald A Watson
Journal: J Am Chem Soc Date: 2017-06-01 Impact factor: 15.419

5 in total

Review 1. Cross-Coupling of Heteroatomic Electrophiles.

Authors: Katerina M Korch; Donald A Watson
Journal: Chem Rev Date: 2019-06-11 Impact factor: 60.622

2. Stereoselective Synthesis of Cis- and Trans-Tetrasubstituted Vinyl Silanes Using a Silyl-Heck Strategy and Hiyama Conditions for Their Cross-Coupling.

Authors: Michael F Wisthoff; Sarah B Pawley; Andrew P Cinderella; Donald A Watson
Journal: J Am Chem Soc Date: 2020-06-30 Impact factor: 15.419