Literature DB >> 11672033

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

Brian H. Ridgway1, K. A. Woerpel.   

Abstract

Deuterium-labeling experiments demonstrate that the transmetalation step of the Suzuki coupling reaction of alkylboranes and alpha-iodoenones proceeds with retention of stereochemistry.

Entities:  

Year:  1998        PMID： 11672033     DOI： 10.1021/jo970803d

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  20 in total

1.  Stereospecific cross-coupling of secondary alkyl β-trifluoroboratoamides.

Authors:  Deidre L Sandrock; Ludivine Jean-Gérard; Cheng-yi Chen; Spencer D Dreher; Gary A Molander
Journal:  J Am Chem Soc       Date:  2010-11-15       Impact factor: 15.419

Review 2.  Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners.

Authors:  Ranjan Jana; Tejas P Pathak; Matthew S Sigman
Journal:  Chem Rev       Date:  2011-02-14       Impact factor: 60.622

3.  New directing groups for metal-catalyzed asymmetric carbon-carbon bond-forming processes: stereoconvergent alkyl-alkyl Suzuki cross-couplings of unactivated electrophiles.

Authors:  Ashraf Wilsily; Francesco Tramutola; Nathan A Owston; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2012-03-26       Impact factor: 15.419

4.  Probing the Electronic Demands of Transmetalation in the Palladium-Catalyzed Cross-Coupling of Arylsilanolates.

Authors:  Scott E Denmark; Russell C Smith; Wen-Tau T Chang
Journal:  Tetrahedron       Date:  2011-06-17       Impact factor: 2.457

5.  Stereospecific cross-coupling of secondary organotrifluoroborates: potassium 1-(benzyloxy)alkyltrifluoroborates.

Authors:  Gary A Molander; Steven R Wisniewski
Journal:  J Am Chem Soc       Date:  2012-10-01       Impact factor: 15.419

6.  Two metals are better than one in the gold catalyzed oxidative heteroarylation of alkenes.

Authors:  Ekaterina Tkatchouk; Neal P Mankad; Diego Benitez; William A Goddard; F Dean Toste
Journal:  J Am Chem Soc       Date:  2011-08-23       Impact factor: 15.419

7.  Retention or inversion in stereospecific nickel-catalyzed cross-coupling of benzylic carbamates with arylboronic esters: control of absolute stereochemistry with an achiral catalyst.

Authors:  Michael R Harris; Luke E Hanna; Margaret A Greene; Curtis E Moore; Elizabeth R Jarvo
Journal:  J Am Chem Soc       Date:  2013-02-22       Impact factor: 15.419

8.  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

9.  Mechanistic duality in palladium-catalyzed cross-coupling reactions of aryldimethylsilanolates. intermediacy of an 8-Si-4 arylpalladium(II) silanolate.

Authors:  Scott E Denmark; Russell C Smith
Journal:  J Am Chem Soc       Date:  2010-02-03       Impact factor: 15.419

10.  Synthesis and Suzuki-Miyaura Cross-Coupling of Enantioenriched Secondary Potassium β-Trifluoroboratoamides: Catalytic, Asymmetric Conjugate Addition of Bisboronic Acid and Tetrakis(dimethylamino)diboron to α,β-Unsaturated Carbonyl Compounds.

Authors:  Gary A Molander; Steven R Wisniewski; Mona Hosseini-Sarvari
Journal:  Adv Synth Catal       Date:  2013-10-11       Impact factor: 5.837
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