Literature DB >> 21077687

Stereospecific cross-coupling of secondary alkyl β-trifluoroboratoamides.

Deidre L Sandrock1, Ludivine Jean-Gérard, Cheng-yi Chen, Spencer D Dreher, Gary A Molander.   

Abstract

The stereospecific cross-coupling of enantioenriched nonbenzylic secondary alkyl boron compounds has been achieved. The high selectivity toward product formation over an undesired β-H elimination pathway is achieved via an intramolecular coordination of an ancillary carbonyl to the metal center in the diorganopalladium intermediate.

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Year:  2010        PMID： 21077687      PMCID： PMC3045699          DOI： 10.1021/ja108949w

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


  35 in total

1.  Iron(III) salen-type catalysts for the cross-coupling of aryl Grignards with alkyl halides bearing beta-hydrogens.

Authors:  Robin B Bedford; Duncan W Bruce; Robert M Frost; John W Goodby; Michael Hird
Journal:  Chem Commun (Camb)       Date:  2004-10-27       Impact factor: 6.222

2.  Transmetalation of Alkylboranes to Palladium in the Suzuki Coupling Reaction Proceeds with Retention of Stereochemistry.

Authors:  Brian H. Ridgway; K. A. Woerpel
Journal:  J Org Chem       Date:  1998-02-06       Impact factor: 4.354

3.  Alkylboranes in the Suzuki-Miyaura Coupling: Stereochemical and Mechanistic Studies.

Authors:  Karl Matos; John A. Soderquist
Journal:  J Org Chem       Date:  1998-02-06       Impact factor: 4.354

4.  Phosphaadamantanes as ligands for palladium catalyzed cross-coupling chemistry: library synthesis, characterization, and screening in the Suzuki coupling of alkyl halides and tosylates containing beta-hydrogens with boronic acids and alkylboranes.

Authors:  Tim Brenstrum; David A Gerristma; George M Adjabeng; Christopher S Frampton; James Britten; Alan J Robertson; James McNulty; Alfredo Capretta
Journal:  J Org Chem       Date:  2004-10-29       Impact factor: 4.354

5.  Stille cross-couplings of unactivated secondary alkyl halides using monoorganotin reagents.

Authors:  David A Powell; Toshihide Maki; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2005-01-19       Impact factor: 15.419

6.  Stille coupling of stereochemically defined alpha-sulfonamidoorganostannanes.

Authors:  Kevin W Kells; J Michael Chong
Journal:  J Am Chem Soc       Date:  2004-12-08       Impact factor: 15.419

7.  Iron-catalyzed Grignard cross-coupling with alkyl halides possessing beta-hydrogens.

Authors:  Takashi Nagano; Tamio Hayashi
Journal:  Org Lett       Date:  2004-04-15       Impact factor: 6.005

8.  Air stable, sterically hindered ferrocenyl dialkylphosphines for palladium-catalyzed C[bond]C, C[bond]N, and C[bond]O bond-forming cross-couplings.

Authors:  Noriyasu Kataoka; Quinetta Shelby; James P Stambuli; John F Hartwig
Journal:  J Org Chem       Date:  2002-08-09       Impact factor: 4.354

9.  Synthesis of aromatic bisabolene natural products via palladium-catalyzed cross-couplings of organozinc reagents.

Authors:  James R Vyvyan; Celeste Loitz; Ryan E Looper; Cheryl S Mattingly; Emily A Peterson; Steven T Staben
Journal:  J Org Chem       Date:  2004-04-02       Impact factor: 4.354

10.  Iron-catalyzed cross-coupling of primary and secondary alkyl halides with aryl grignard reagents.

Authors:  Masaharu Nakamura; Keiko Matsuo; Shingo Ito; Eiichi Nakamura
Journal:  J Am Chem Soc       Date:  2004-03-31       Impact factor: 15.419
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  54 in total

1.  A General, Simple Catalyst for Enantiospecific Cross Couplings of Benzylic Ammonium Triflates and Boronic Acids: No Phosphine Ligand Required.

Authors:  Danielle M Shacklady-McAtee; Kelsey M Roberts; Corey H Basch; Ye-Geun Song; Mary P Watson
Journal:  Tetrahedron       Date:  2014-07-08       Impact factor: 2.457

2.  Palladium-catalyzed allylic substitution with (η6-arene-CH2Z)Cr(CO)(3)-based nucleophiles.

Authors:  Jiadi Zhang; Corneliu Stanciu; Beibei Wang; Mahmud M Hussain; Chao-Shan Da; Patrick J Carroll; Spencer D Dreher; Patrick J Walsh
Journal:  J Am Chem Soc       Date:  2011-11-29       Impact factor: 15.419

Review 3.  Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds.

Authors:  Alan H Cherney; Nathaniel T Kadunce; Sarah E Reisman
Journal:  Chem Rev       Date:  2015-08-13       Impact factor: 60.622

4.  Structural, Kinetic, and Computational Characterization of the Elusive Arylpalladium(II)boronate Complexes in the Suzuki-Miyaura Reaction.

Authors:  Andy A Thomas; Hao Wang; Andrew F Zahrt; Scott E Denmark
Journal:  J Am Chem Soc       Date:  2017-03-07       Impact factor: 15.419

5.  Copper-catalyzed β-boration of α,β-unsaturated carbonyl compounds with tetrahydroxydiborane.

Authors:  Gary A Molander; Silas A McKee
Journal:  Org Lett       Date:  2011-08-05       Impact factor: 6.005

6.  Enantioselective desymmetrization via carbonyl-directed catalytic asymmetric hydroboration and Suzuki-Miyaura cross-coupling.

Authors:  Gia L Hoang; Zhao-Di Yang; Sean M Smith; Rhitankar Pal; Judy L Miska; Damaris E Pérez; Libbie S W Pelter; Xiao Cheng Zeng; James M Takacs
Journal:  Org Lett       Date:  2015-02-02       Impact factor: 6.005

7.  Complementary regioselectivity in Rh(III)-catalyzed insertions of potassium vinyltrifluoroborate via C-H activation: preparation and use of 4-trifluoroboratotetrahydroisoquinolones.

Authors:  Marc Presset; Daniel Oehlrich; Frederik Rombouts; Gary A Molander
Journal:  Org Lett       Date:  2013-03-15       Impact factor: 6.005

8.  Nickel-catalyzed cross-couplings of benzylic pivalates with arylboroxines: stereospecific formation of diarylalkanes and triarylmethanes.

Authors:  Qi Zhou; Harathi D Srinivas; Srimoyee Dasgupta; Mary P Watson
Journal:  J Am Chem Soc       Date:  2013-02-20       Impact factor: 15.419

9.  Mechanistic Studies of Azaphilic versus Carbophilic Activation by Gold(I) in the Gold/Palladium Dual-Catalyzed Rearrangement of Alkenyl Vinyl Aziridines.

Authors:  Joshua J Hirner; Katrina E Roth; Yili Shi; Suzanne A Blum
Journal:  Organometallics       Date:  2012-10-08       Impact factor: 3.876

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

Authors:  Jian He; Heng Jiang; Ryosuke Takise; Ru-Yi Zhu; Gang Chen; Hui-Xiong Dai; T G Murali Dhar; Jun Shi; Hao Zhang; Peter T W Cheng; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2015-11-27       Impact factor: 15.336
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