Literature DB >> 31062812

Reactions of organoboron compounds enabled by catalyst-promoted metalate shifts.

Sheila Namirembe1, James P Morken.   

Abstract

This tutorial review describes recent developments in catalytic reaction design that involve catalyst-promoted 1,2-metalate shifts as a critical part of the reaction mechanism. Issues pertaining to catalysis, stereoselectivity, and reaction mechanism are discussed.

Entities:  

Year:  2019        PMID： 31062812      PMCID： PMC7053661          DOI： 10.1039/c9cs00180h

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN： 0306-0012            Impact factor:   54.564


  18 in total

1.  Studies directed toward the synthesis of prostaglandins. Useful boron-mediated olefin syntheses.

Authors:  D A Evans; T C Crawford; R C Thomas; J A Walker
Journal:  J Org Chem       Date:  1976-12-10       Impact factor: 4.354

2.  Enantioselective Construction of Tertiary Boronic Esters by Conjunctive Cross-Coupling.

Authors:  Jesse A Myhill; Liang Zhang; Gabriel J Lovinger; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2018-08-29       Impact factor: 15.336

3.  Transition-Metal-Free Suzuki-Type Cross-Coupling Reaction of Benzyl Halides and Boronic Acids via 1,2-Metalate Shift.

Authors:  Zhiqi He; Feifei Song; Huan Sun; Yong Huang
Journal:  J Am Chem Soc       Date:  2018-02-05       Impact factor: 15.419

4.  Enantioselective, Lewis Base-Catalyzed Carbosulfenylation of Alkenylboronates by 1,2-Boronate Migration.

Authors:  Zhonglin Tao; Kevin A Robb; Jesse L Panger; Scott E Denmark
Journal:  J Am Chem Soc       Date:  2018-11-09       Impact factor: 15.419

5.  Nickel-Catalyzed Enantioselective Conjunctive Cross-Coupling of 9-BBN Borates.

Authors:  Matteo Chierchia; Chunyin Law; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2017-08-17       Impact factor: 15.336

6.  Mechanistic, crystallographic, and computational studies on the catalytic, enantioselective sulfenofunctionalization of alkenes.

Authors:  Scott E Denmark; Eduard Hartmann; David J P Kornfilt; Hao Wang
Journal:  Nat Chem       Date:  2014-11-10       Impact factor: 24.427

7.  Ni-Catalyzed Enantioselective Conjunctive Coupling with C(sp3) Electrophiles: A Radical-Ionic Mechanistic Dichotomy.

Authors:  Gabriel J Lovinger; James P Morken
Journal:  J Am Chem Soc       Date:  2017-11-20       Impact factor: 15.419

8.  Stereoselective synthesis of (E)-(trisubstituted alkenyl)borinic esters: stereochemistry reversed by ligand in the palladium-catalyzed reaction of alkynylborates with aryl halides.

Authors:  Naoki Ishida; Yasuhiro Shimamoto; Masahiro Murakami
Journal:  Org Lett       Date:  2009-12-03       Impact factor: 6.005

9.  Diastereoselective and Enantioselective Conjunctive Cross-Coupling Enabled by Boron Ligand Design.

Authors:  Jesse A Myhill; Christopher A Wilhelmsen; Liang Zhang; James P Morken
Journal:  J Am Chem Soc       Date:  2018-11-06       Impact factor: 15.419

10.  Carbopalladation of C-C σ-bonds enabled by strained boronate complexes.

Authors:  Alexander Fawcett; Tobias Biberger; Varinder K Aggarwal
Journal:  Nat Chem       Date:  2018-12-10       Impact factor: 24.427
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  23 in total

1.  Catalytic Enantioselective Synthesis of anti-Vicinal Silylboronates by Conjunctive Cross-Coupling.

Authors:  Yan Meng; Ziyin Kong; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2020-03-19       Impact factor: 15.336

2.  Stereoselectivity in Pd-catalysed cross-coupling reactions of enantioenriched nucleophiles.

Authors:  Xinghua Ma; Benjamin Murray; Mark R Biscoe
Journal:  Nat Rev Chem       Date:  2020-09-24       Impact factor: 34.035

3.  Transition Metal Free sp3-sp3 carbon-carbon coupling between Benzylboronic Esters and Alkyl Bromides.

Authors:  Richard W Russell; Timothy J Barker
Journal:  European J Org Chem       Date:  2021-04-23

4.  Enantioselective catalytic 1,2-boronate rearrangements.

Authors:  Hayden A Sharma; Jake Z Essman; Eric N Jacobsen
Journal:  Science       Date:  2021-11-04       Impact factor: 47.728

5.  Cu-Catalyzed Cross-Coupling of Benzylboronic Esters and Epoxides.

Authors:  Sophia G Gierszal; Timothy J Barker
Journal:  Tetrahedron Lett       Date:  2021-09-07       Impact factor: 2.032

6.  Alkyl Group Migration in Ni-Catalyzed Conjunctive Coupling with C(sp3) Electrophiles: Reaction Development and Application to Targets of Interest.

Authors:  Seung Moh Koo; Alex J Vendola; Sarah Noemi Momm; James P Morken
Journal:  Org Lett       Date:  2020-01-07       Impact factor: 6.005

7.  Enantioselective Allylation of Alkenyl Boronates Promotes a 1,2-Metalate Rearrangement with 1,3-Diastereocontrol.

Authors:  Colton R Davis; Irungu K Luvaga; Joseph M Ready
Journal:  J Am Chem Soc       Date:  2021-03-23       Impact factor: 15.419

8.  Mechanism of Z-Selective Hydroalkylation of Terminal Alkynes.

Authors:  Mitchell T Lee; Gojko Lalic
Journal:  J Am Chem Soc       Date:  2021-09-29       Impact factor: 16.383

Review 9.  Radical-Induced 1,2-Migrations of Boron Ate Complexes.

Authors:  Marvin Kischkewitz; Florian W Friese; Armido Studer
Journal:  Adv Synth Catal       Date:  2020-02-21       Impact factor: 5.837

10.  Radical Aryl Migration from Boron to Carbon.

Authors:  Dinghai Wang; Christian Mück-Lichtenfeld; Constantin G Daniliuc; Armido Studer
Journal:  J Am Chem Soc       Date:  2021-06-20       Impact factor: 15.419
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