Literature DB >> 30893498

Catalytic Conjunctive Coupling of Carboxylic Acid Derivatives with 9-BBN-Derived Ate Complexes.

Chunyin Law1, Yan Meng1, Seung Moh Koo1, James P Morken1.   

Abstract

β-Boryl carbonyl compounds are produced by a Ni-catalyzed cross-coupling of vinylboron "ate" complexes and acid chloride or acid anhydride electrophiles. The reactions are efficient, being complete in as little as two minutes, and can be applied to a broad range of substrates.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  boron; catalysis; conjugative coupling; cross-coupling; nickel

Year:  2019        PMID： 30893498      PMCID： PMC6502666          DOI： 10.1002/anie.201901927

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  38 in total

1.  Copper(I)-secondary diamine complex-catalyzed enantioselective conjugate boration of linear β,β-disubstituted enones.

Authors:  I-Hon Chen; Motomu Kanai; Masakatsu Shibasaki
Journal:  Org Lett       Date:  2010-09-17       Impact factor: 6.005

2.  Ligand-dependent catalytic cycle and role of styrene in nickel-catalyzed anhydride cross-coupling: evidence for turnover-limiting reductive elimination.

Authors:  Jeffrey B Johnson; Eric A Bercot; John M Rowley; Geoffrey W Coates; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2007-02-13       Impact factor: 15.419

3.  Enantioselective conjugate borylation.

Authors:  Julia A Schiffner; Kristine Müther; Martin Oestreich
Journal:  Angew Chem Int Ed Engl       Date:  2010-02-08       Impact factor: 15.336

4.  Enantioselective synthesis of boron-substituted quaternary carbons by NHC-Cu-catalyzed boronate conjugate additions to unsaturated carboxylic esters, ketones, or thioesters.

Authors:  Jeannette M O'Brien; Kang-sang Lee; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2010-08-11       Impact factor: 15.419

5.  A unique catalyst effects the rapid room-temperature cross-coupling of organozinc reagents with carboxylic acid fluorides, chlorides, anhydrides, and thioesters.

Authors:  Yongda Zhang; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2004-12-15       Impact factor: 15.419

6.  Iterative approach to oligo(arylenevinylene)s containing tetrasubstituted vinylene units.

Authors:  Naoki Ishida; Yasuhiro Shimamoto; Masahiro Murakami
Journal:  Org Lett       Date:  2010-07-16       Impact factor: 6.005

7.  Migratory aptitudes of simple alkyl groups in the anionotropic rearrangement of quaternary chloromethyl borate species: a combined experimental and theoretical investigation.

Authors:  Andrea Bottoni; Marco Lombardo; Andrea Neri; Claudio Trombini
Journal:  J Org Chem       Date:  2003-05-02       Impact factor: 4.354

8.  Synthesis of amine-borane intramolecular complexes through palladium-catalyzed rearrangement of ammonioalkynyltriarylborates.

Authors:  Naoki Ishida; Mizuna Narumi; Masahiro Murakami
Journal:  Org Lett       Date:  2008-02-14       Impact factor: 6.005

9.  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

10.  Catalytic asymmetric synthesis of chiral tertiary organoboronic esters through conjugate boration of beta-substituted cyclic enones.

Authors:  I-Hon Chen; Liang Yin; Wataru Itano; Motomu Kanai; Masakatsu Shibasaki
Journal:  J Am Chem Soc       Date:  2009-08-26       Impact factor: 15.419
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  7 in total

1.  Enantioselective Radical Addition/Cross-Coupling of Organozinc Reagents, Alkyl Iodides, and Alkenyl Boron Reagents.

Authors:  Matteo Chierchia; Peilin Xu; Gabriel J Lovinger; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2019-08-28       Impact factor: 15.336

2.  Enantioselective Synthesis of Tertiary β-Boryl Amides by Conjunctive Cross-Coupling of Alkenyl Boronates and Carbamoyl Chlorides.

Authors:  Christopher A Wilhelmsen; Xuntong Zhang; Jesse A Myhill; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2022-02-18       Impact factor: 15.336

3.  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

4.  Total Synthesis of the Spliceosome Modulator Pladienolide B via Asymmetric Alcohol-Mediated syn- and anti-Diastereoselective Carbonyl Crotylation.

Authors:  Minjin Yoo; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2021-05-11       Impact factor: 16.823

5.  Synthesis of 1,3-Bis-(boryl)alkanes through Boronic Ester Induced Consecutive Double 1,2-Migration.

Authors:  Cai You; Armido Studer
Journal:  Angew Chem Int Ed Engl       Date:  2020-08-07       Impact factor: 15.336

6.  Three-component 1,2-carboamination of vinyl boronic esters via amidyl radical induced 1,2-migration.

Authors:  Cai You; Armido Studer
Journal:  Chem Sci       Date:  2021-11-16       Impact factor: 9.825

7.  Deoxygenative α-alkylation and α-arylation of 1,2-dicarbonyls.

Authors:  Shengfei Jin; Hang T Dang; Graham C Haug; Viet D Nguyen; Hadi D Arman; Oleg V Larionov
Journal:  Chem Sci       Date:  2020-07-01       Impact factor: 9.825
  7 in total

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