Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 Palladium-catalyzed hydroarylation of 1,3-dienes with boronic esters via reductive formation of pi-allyl palladium intermediates under oxidative conditions.

Literature DB >> 20608751

Palladium-catalyzed hydroarylation of 1,3-dienes with boronic esters via reductive formation of pi-allyl palladium intermediates under oxidative conditions.

Abstract

A palladium-catalyzed reductive cross-coupling of 1,3-dienes with boronic esters in which a pi-allyl Pd species is generated directly from a 1,3-diene via a Pd-catalyzed aerobic alcohol oxidation is reported. Both the scope of the process and the origin of a highly selective 1,2-addition are discussed.

Entities: Chemical Disease

Mesh：

Substances：

Year: 2010 PMID： 20608751 PMCID： PMC2911521 DOI： 10.1021/ja105010t

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

23 in total

1. Sequential hydrocarbon functionalization: allylic C-H oxidation/vinylic C-H arylation.

Authors: Jared H Delcamp; M Christina White
Journal: J Am Chem Soc Date: 2006-11-29 Impact factor: 15.419

2. Quantitatively correlating the effect of ligand-substituent size in asymmetric catalysis using linear free energy relationships.

Authors: Jeremie J Miller; Matthew S Sigman
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

3. Primary tert- and sec-allylamines via palladium-catalyzed hydroamination and allylic substitution with hydrazine and hydroxylamine derivatives.

Authors: Adam M Johns; Zhijian Liu; John F Hartwig
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

4. Catalytic intermolecular linear allylic C-H amination via heterobimetallic catalysis.

Authors: Sean A Reed; M Christina White
Journal: J Am Chem Soc Date: 2008-02-27 Impact factor: 15.419

5. Highly selective stereodivergent synthesis of separable amide rotamers, by using Pd chemistry, and their thermodynamic behavior.

Authors: Nobutaka Ototake; Masashi Nakamura; Yasuo Dobashi; Haruhiko Fukaya; Osamu Kitagawa
Journal: Chemistry Date: 2009 Impact factor: 5.236

6. Palladium-catalyzed intermolecular aerobic oxidative amination of terminal alkenes: efficient synthesis of linear allylamine derivatives.

Authors: Guosheng Liu; Guoyin Yin; Liang Wu
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

7. (eta(3)-Allyl)palladium Complexes Bearing Diphosphinidenecyclobutene Ligands: Highly Active Catalysts for the Hydroamination of 1,3-Dienes This work was supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Science, Sports and Culture, Japan.

Authors: Tatsuya Minami; Hideyuki Okamoto; Shintaro Ikeda; Rika Tanaka; Fumiyuki Ozawa; Masaaki Yoshifuji
Journal: Angew Chem Int Ed Engl Date: 2001-12-03 Impact factor: 15.336

8. Cross-coupling of aromatic bromides with allylic silanolate salts.

Authors: Scott E Denmark; Nathan S Werner
Journal: J Am Chem Soc Date: 2008-12-03 Impact factor: 15.419

9. Palladium-catalyzed hydroalkylation of styrenes with organozinc reagents to form carbon-carbon sp3-sp3 bonds under oxidative conditions.

Authors: Kaveri Balan Urkalan; Matthew S Sigman
Journal: J Am Chem Soc Date: 2009-12-23 Impact factor: 15.419

10. A sulfoxide-promoted, catalytic method for the regioselective synthesis of allylic acetates from monosubstituted olefins via C-H oxidation.

Authors: Mark S Chen; M Christina White
Journal: J Am Chem Soc Date: 2004-02-11 Impact factor: 15.419

18 in total

1. Palladium-catalyzed hydrofunctionalization of vinyl phenol derivatives with heteroaromatics.

Authors: Tejas P Pathak; Matthew S Sigman
Journal: Org Lett Date: 2011-04-21 Impact factor: 6.005

2. Palladium(II)-catalyzed enantio- and diastereoselective synthesis of pyrrolidine derivatives.

Authors: Ranjan Jana; Tejas P Pathak; Katrina H Jensen; Matthew S Sigman
Journal: Org Lett Date: 2012-08-08 Impact factor: 6.005

3. Mechanism and Selectivity in the Pd-Catalyzed Difunctionalization of Isoprene.

Authors: Liping Xu; Xin Zhang; Matthew S McCammant; Matthew S Sigman; Yun-Dong Wu; Olaf Wiest
Journal: J Org Chem Date: 2016-08-19 Impact factor: 4.354

4. A palladium-catalyzed three-component cross-coupling of conjugated dienes or terminal alkenes with vinyl triflates and boronic acids.

Authors: Longyan Liao; Ranjan Jana; Kaveri Balan Urkalan; Matthew S Sigman
Journal: J Am Chem Soc Date: 2011-03-30 Impact factor: 15.419

5. Asymmetric palladium-catalyzed hydroarylation of styrenes and dienes.

Authors: Susanne M Podhajsky; Yasumasa Iwai; Amanda Cook-Sneathen; Matthew S Sigman
Journal: Tetrahedron Date: 2011-06-17 Impact factor: 2.457

6. Palladium-Catalyzed 1,3-Difunctionalization Using Terminal Alkenes with Alkenyl Nonaflates and Aryl Boronic Acids.

Authors: Matthew S McCammant; Takashi Shigeta; Matthew S Sigman
Journal: Org Lett Date: 2016-03-28 Impact factor: 6.005

7. Anti-Markovnikov hydroalkylation of allylic amine derivatives via a palladium-catalyzed reductive cross-coupling reaction.

Authors: Ryan J DeLuca; Matthew S Sigman
Journal: J Am Chem Soc Date: 2011-07-11 Impact factor: 15.419

8. Palladium-catalyzed 1,4-difunctionalization of butadiene to form skipped polyenes.

Authors: Matthew S McCammant; Longyan Liao; Matthew S Sigman
Journal: J Am Chem Soc Date: 2013-03-12 Impact factor: 15.419

9. Palladium-catalyzed allylic cross-coupling reactions of primary and secondary homoallylic electrophiles.

Authors: Benjamin J Stokes; Susanne M Opra; Matthew S Sigman
Journal: J Am Chem Soc Date: 2012-07-06 Impact factor: 15.419

10. Pd(Quinox)-Catalyzed Allylic Relay Suzuki Reactions of Secondary Homostyrenyl Tosylates via Alkene-Assisted Oxidative Addition.

Authors: Benjamin J Stokes; Amanda J Bischoff; Matthew S Sigman
Journal: Chem Sci Date: 2014-06-01 Impact factor: 9.825