Literature DB >> 19301820

Cross coupling reactions of chiral secondary organoboronic esters with retention of configuration.

Daisuke Imao1, Ben W Glasspoole, Véronique S Laberge, Cathleen M Crudden.   

Abstract

We report the first example of a coupling reaction of chiral secondary boronic esters generated by the hydroboration of vinyl arenes. In order for the reaction to take place in high yields, the use of silver oxide as a base and the presence of at least 8 equiv of triphenyl phosphine per Pd are required. The reaction proceeds with >90% retention of configuration in all cases except one. Remarkably, the linear boronate ester does not react under these conditions.

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Year:  2009        PMID： 19301820     DOI： 10.1021/ja8094075

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


  77 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.  Cross-coupling: The final frontier.

Authors:  Ben W Glasspoole; Cathleen M Crudden
Journal:  Nat Chem       Date:  2011-11-23       Impact factor: 24.427

3.  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 4.  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

5.  Nickel-Catalyzed Asymmetric Reductive Cross-Coupling To Access 1,1-Diarylalkanes.

Authors:  Kelsey E Poremba; Nathaniel T Kadunce; Naoyuki Suzuki; Alan H Cherney; Sarah E Reisman
Journal:  J Am Chem Soc       Date:  2017-04-13       Impact factor: 15.419

6.  Ligand-accelerated ortho-C-H alkylation of arylcarboxylic acids using alkyl boron reagents.

Authors:  Peter S Thuy-Boun; Giorgio Villa; Devin Dang; Paul Richardson; Shun Su; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2013-11-08       Impact factor: 15.419

7.  Pd(0)-catalyzed 1,1-diarylation of ethylene and allylic carbonates.

Authors:  Vaneet Saini; Longyan Liao; Qiaofeng Wang; Ranjan Jana; Matthew S Sigman
Journal:  Org Lett       Date:  2013-09-18       Impact factor: 6.005

8.  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

9.  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

10.  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
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