Literature DB >> 31666755

Transition-Metal-Catalyzed Alkyl Heck-Type Reactions.

Daria Kurandina1, Padon Chuentragool1, Vladimir Gevorgyan1.   

Abstract

The Heck reaction is one of the most reliable and useful strategies for the construction of C-C bonds in organic synthesis. However, in contrast to the well-established aryl Heck reaction, the analogous reaction employing alkyl electrophiles is much less developed. Significant progress in this area was recently achieved by merging radical-mediated and transition-metal-catalyzed approaches. This review summarizes the advances in alkyl Heck-type reactions from its discovery early in the 1970s up until the end of 2018.

Entities:  

Keywords:  Heck reaction; alkenes; alkyl halides; cross-coupling; transition-metal catalysis

Year:  2019        PMID: 31666755      PMCID: PMC6820999          DOI: 10.1055/s-0037-1611659

Source DB:  PubMed          Journal:  Synthesis (Stuttg)        ISSN: 0039-7881            Impact factor:   3.157


  53 in total

1.  Photocatalytic synthesis of allylic trifluoromethyl substituted styrene derivatives in batch and flow.

Authors:  Lukas M Kreis; Simon Krautwald; Nicole Pfeiffer; Rainer E Martin; Erick M Carreira
Journal:  Org Lett       Date:  2013-03-21       Impact factor: 6.005

2.  Palladium-Catalyzed 6-Endo Selective Alkyl-Heck Reactions: Access to 5-Phenyl-1,2,3,6-tetrahydropyridine Derivatives.

Authors:  Xu Dong; Ying Han; Fachao Yan; Qing Liu; Ping Wang; Kexun Chen; Yueyun Li; Zengdian Zhao; Yunhui Dong; Hui Liu
Journal:  Org Lett       Date:  2016-07-13       Impact factor: 6.005

3.  Palladium-Catalyzed Carbocyclizations of Unactivated Alkyl Bromides with Alkenes Involving Auto-tandem Catalysis.

Authors:  Alexander R O Venning; Megan R Kwiatkowski; Joan E Roque Peña; Brendan C Lainhart; Akil A Guruparan; Erik J Alexanian
Journal:  J Am Chem Soc       Date:  2017-08-14       Impact factor: 15.419

4.  Palladium-catalyzed, asymmetric Mizoroki-Heck reaction of benzylic electrophiles using phosphoramidites as chiral ligands.

Authors:  Zhigang Yang; Jianrong Zhou
Journal:  J Am Chem Soc       Date:  2012-07-11       Impact factor: 15.419

5.  Amine-Controlled Divergent Reaction: Iminolactonization and Olefination in the Presence of a Cu(I) Catalyst.

Authors:  Takashi Nishikata; Kohei Itonaga; Norihiro Yamaguchi; Michinori Sumimoto
Journal:  Org Lett       Date:  2017-05-10       Impact factor: 6.005

6.  Palladium-catalyzed intermolecular Heck reaction of alkyl halides.

Authors:  Yinjun Zou; Jianrong Steve Zhou
Journal:  Chem Commun (Camb)       Date:  2014-04-11       Impact factor: 6.222

7.  Intermolecular Photocatalyzed Heck-like Coupling of Unactivated Alkyl Bromides by a Dinuclear Gold Complex.

Authors:  Jin Xie; Jian Li; Vanessa Weingand; Matthias Rudolph; A Stephen K Hashmi
Journal:  Chemistry       Date:  2016-08-01       Impact factor: 5.236

8.  Ni-catalyzed cascade formation of C(sp3)--C(sp3) bonds by cyclization and cross-coupling reactions of iodoalkanes with alkyl zinc halides.

Authors:  Vilas B Phapale; Elena Buñuel; Miguel García-Iglesias; Diego J Cárdenas
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

9.  Irradiation-Induced Palladium-Catalyzed Decarboxylative Heck Reaction of Aliphatic N-(Acyloxy)phthalimides at Room Temperature.

Authors:  Guang-Zu Wang; Rui Shang; Yao Fu
Journal:  Org Lett       Date:  2018-01-18       Impact factor: 6.005

10.  Nickel-catalyzed Negishi arylations of propargylic bromides: a mechanistic investigation.

Authors:  Nathan D Schley; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2014-11-17       Impact factor: 15.419

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  12 in total

1.  Photoinduced Palladium-Catalyzed Carbofunctionalization of Conjugated Dienes Proceeding via Radical-Polar Crossover Scenario: 1,2-Aminoalkylation and Beyond.

Authors:  Kelvin Pak Shing Cheung; Daria Kurandina; Tetsuji Yata; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2020-05-19       Impact factor: 15.419

2.  Excited-State Palladium-Catalyzed Radical Migratory Mizoroki-Heck Reaction Enables C2-Alkenylation of Carbohydrates.

Authors:  Wang Yao; Gaoyuan Zhao; Yue Wu; Lin Zhou; Upasana Mukherjee; Peng Liu; Ming-Yu Ngai
Journal:  J Am Chem Soc       Date:  2022-02-21       Impact factor: 15.419

3.  Contrasteric coupling of allenes and tetrahydroisoquinolines by iron-catalysed allenic C(sp2)-H functionalisation.

Authors:  Yue Xia; Nicholas W Wade; Philip N Palermo; Yidong Wang; Yi-Ming Wang
Journal:  Chem Commun (Camb)       Date:  2021-12-09       Impact factor: 6.222

4.  Visible Light Induced Brønsted Acid Assisted Pd-Catalyzed Alkyl Heck Reaction of Diazo Compounds and N-Tosylhydrazones.

Authors:  Ziyan Zhang; Nikita Kvasovs; Anastasiia Dubrovina; Vladimir Gevorgyan
Journal:  Angew Chem Int Ed Engl       Date:  2021-11-23       Impact factor: 15.336

5.  Asymmetric Photocatalysis Enabled by Chiral Organocatalysts.

Authors:  Wang Yao; Emmanuel A Bazan Bergamino; Ming-Yu Ngai
Journal:  ChemCatChem       Date:  2021-10-21       Impact factor: 5.497

6.  Three-Component Visible-Light-Induced Palladium-Catalyzed 1,2-Alkyl Carbamoylation/Cyanation of Alkenes.

Authors:  Xiangqing Jia; Ziyan Zhang; Vladimir Gevorgyan
Journal:  ACS Catal       Date:  2021-10-15       Impact factor: 13.700

7.  Divergent regioselective Heck-type reaction of unactivated alkenes and N-fluoro-sulfonamides.

Authors:  Chunyang Zhao; Yang Li; Yujiao Dong; Miao Li; Dan Xia; Shuangqiu Gao; Qian Zhang; Qun Liu; Wei Guan; Junkai Fu
Journal:  Nat Commun       Date:  2022-10-22       Impact factor: 17.694

8.  Dealkenylative Alkenylation: Formal σ-Bond Metathesis of Olefins.

Authors:  Manisha Swain; Gusein Sadykhov; Ruoxi Wang; Ohyun Kwon
Journal:  Angew Chem Int Ed Engl       Date:  2020-08-28       Impact factor: 15.336

9.  Excited-State Palladium-Catalyzed 1,2-Spin-Center Shift Enables Selective C-2 Reduction, Deuteration, and Iodination of Carbohydrates.

Authors:  Gaoyuan Zhao; Wang Yao; Jaclyn N Mauro; Ming-Yu Ngai
Journal:  J Am Chem Soc       Date:  2021-01-19       Impact factor: 15.419

10.  Pd-catalyzed formal Mizoroki-Heck coupling of unactivated alkyl chlorides.

Authors:  Geun Seok Lee; Daeun Kim; Soon Hyeok Hong
Journal:  Nat Commun       Date:  2021-02-12       Impact factor: 14.919

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