Literature DB >> 29130026

Recent Developments in Pd(0)-Catalyzed Alkene Carboheterofunctionalization Reactions.

Zachary J Garlets1, Derick R White1, John P Wolfe1.   

Abstract

This review summarizes recent developments in palladium-catalyzed alkene carboalkoxylation and carboamination reactions. New synthetic methods that have been reported in the past four years are described, along with mechanistic issues and the influence of mechanism on product stereochemistry. The applications of these transformations to the synthesis of natural products and other biologically relevant compounds are also discussed.

Entities:  

Keywords:  Alkenes; Carbocycles; Catalysis; Heterocycles; Palladium

Year:  2017        PMID： 29130026      PMCID： PMC5675590          DOI： 10.1002/ajoc.201600577

Source DB:  PubMed          Journal:  Asian J Org Chem        ISSN： 2193-5807            Impact factor:   3.319


  73 in total

1.  The asymmetric intramolecular Heck reaction in natural product total synthesis.

Authors:  Amy B Dounay; Larry E Overman
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

2.  Cascade Pd(II)-catalyzed Wacker lactonization-Heck reaction: rapid assembly of spiranoid lactones.

Authors:  Ghassan Albarghouti; Ramesh Kotikalapudi; David Lankri; Viviana Valerio; Dmitry Tsvelikhovsky
Journal:  Chem Commun (Camb)       Date:  2016-02-21       Impact factor: 6.222

3.  Palladium-catalyzed vicinal amino alcohols synthesis from allyl amines by in situ tether formation and carboetherification.

Authors:  Ugo Orcel; Jerome Waser
Journal:  Angew Chem Int Ed Engl       Date:  2015-02-26       Impact factor: 15.336

4.  Nucleopalladation-initiated oxyalkenylation of alkenes: a strategy to construct functionalized oxygenated heterocycles.

Authors:  Liangbin Huang; Qian Wang; Wanqing Wu; Huanfeng Jiang
Journal:  J Org Chem       Date:  2014-07-29       Impact factor: 4.354

5.  Mild conditions for the synthesis of functionalized pyrrolidines via Pd-catalyzed carboamination reactions.

Authors:  Myra Beaudoin Bertrand; Matthew L Leathen; John P Wolfe
Journal:  Org Lett       Date:  2007-02-01       Impact factor: 6.005

6.  Palladium-Catalyzed Intramolecular Insertion of Alkenes into the Carbon-Nitrogen Bond of β-Lactams.

Authors:  Akira Yada; Satoshi Okajima; Masahiro Murakami
Journal:  J Am Chem Soc       Date:  2015-07-01       Impact factor: 15.419

7.  Influence of catalyst structure and reaction conditions on anti- versus syn-aminopalladation pathways in Pd-catalyzed alkene carboamination reactions of N-allylsulfamides.

Authors:  Ryan M Fornwald; Jonathan A Fritz; John P Wolfe
Journal:  Chemistry       Date:  2014-06-17       Impact factor: 5.236

8.  Palladium-catalyzed synthesis of N-aryl pyrrolidines from gamma-(N-Arylamino) alkenes: evidence for chemoselective alkene insertion into Pd--N bonds.

Authors:  Joshua E Ney; John P Wolfe
Journal:  Angew Chem Int Ed Engl       Date:  2004-07-05       Impact factor: 15.336

9.  The syn/anti-dichotomy in the palladium-catalyzed addition of nucleophiles to alkenes.

Authors:  Pavel Kočovský; Jan-E Bäckvall
Journal:  Chemistry       Date:  2014-11-05       Impact factor: 5.236

10.  Synthesis of substituted 2-aminoimidazoles via Pd-catalyzed alkyne carboamination reactions. Application to the synthesis of preclathridine natural products.

Authors:  Blane P Zavesky; Nicholas R Babij; John P Wolfe
Journal:  Org Lett       Date:  2014-09-08       Impact factor: 6.005
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  20 in total

1.  Catalytic Alkyne Arylation Using Traceless Directing Groups.

Authors:  Jung-Woo Park; Bubwoong Kang; Vy M Dong
Journal:  Angew Chem Int Ed Engl       Date:  2018-09-11       Impact factor: 15.336

2.  Energy Decomposition Analyses Reveal the Origins of Catalyst and Nucleophile Effects on Regioselectivity in Nucleopalladation of Alkenes.

Authors:  Xiaotian Qi; Daniel G Kohler; Kami L Hull; Peng Liu
Journal:  J Am Chem Soc       Date:  2019-07-19       Impact factor: 15.419

3.  Pd-Catalyzed Alkene Diamination Reactions of Nitrogen Electrophiles: Synthesis of Cyclic Guanidines and Ureas Bearing Dialkylaminomethyl Groups.

Authors:  Luke J Peterson; Janelle K Kirsch; John P Wolfe
Journal:  Org Lett       Date:  2018-06-06       Impact factor: 6.005

4.  Cu-Catalyzed Three-Component Carboamination of Alkenes.

Authors:  Samuel N Gockel; Travis L Buchanan; Kami L Hull
Journal:  J Am Chem Soc       Date:  2017-12-28       Impact factor: 15.419

5.  Pd-Catalyzed C-C, C-N, and C-O Bond-Forming Difunctionalization Reactions of Alkenes Bearing Tethered Aryl/Alkenyl Triflates.

Authors:  Derick R White; Evan C Bornowski; John P Wolfe
Journal:  Isr J Chem       Date:  2020-01-24       Impact factor: 3.333

6.  Catalytic, Enantioselective α-Alkylation of Azlactones with Nonconjugated Alkenes by Directed Nucleopalladation.

Authors:  Sri Krishna Nimmagadda; Mingyu Liu; Malkanthi K Karunananda; De-Wei Gao; Omar Apolinar; Jason S Chen; Peng Liu; Keary M Engle
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-27       Impact factor: 15.336

7.  Pd-Catalyzed Alkene Carboheteroarylation Reactions for the Synthesis of 3-Cyclopentylindole Derivatives.

Authors:  Janelle K Kirsch; Jenna L Manske; John P Wolfe
Journal:  J Org Chem       Date:  2018-10-10       Impact factor: 4.354

8.  Synthesis of Phthalans Via Copper-Catalyzed Enantioselective Cyclization/Carboetherification of 2-Vinylbenzyl Alcohols.

Authors:  Dake Chen; Sherry R Chemler
Journal:  Org Lett       Date:  2018-10-11       Impact factor: 6.005

Review 9.  Recent applications of chiral phosphoric acids in palladium catalysis.

Authors:  Van T Tran; Sri Krishna Nimmagadda; Mingyu Liu; Keary M Engle
Journal:  Org Biomol Chem       Date:  2020-01-07       Impact factor: 3.876

10.  Stereocontrolled synthesis of bicyclic ureas and sulfamides via Pd-catalyzed alkene carboamination reactions.

Authors:  Nicholas R Babij; Jordan R Boothe; Grace M McKenna; Ryan M Fornwald; John P Wolfe
Journal:  Tetrahedron       Date:  2019-04-20       Impact factor: 2.457
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