Literature DB >> 31237304

Synergistic palladium/enamine catalysis for asymmetric hydrocarbon functionalization of unactivated alkenes with ketones.

Chiyu Wei1, Xiaohan Ye1, Qingyu Xing1, Yong Hu2, Yan Xie3, Xiaodong Shi1.   

Abstract

Synergistic palladium and enamine catalysis was explored to promote ketone addition to unactivated olefins. A secondary amine-based organocatalyst was identified as the optimal co-catalyst for the directed Pd-catalyzed alkene activation. Furthermore, asymmetric hydrocarbon functionalization of unactivated alkenes was also achieved with good to excellent yield (up to 96% yields) and stereoselectivity (up to 96% ee). This strategy presented an efficient approach to prepare α-branched ketone derivatives under mild conditions.

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Year:  2019        PMID: 31237304      PMCID: PMC6677245          DOI: 10.1039/c9ob01165j

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  37 in total

1.  Palladium-catalyzed intramolecular addition of 1,3-diones to unactivated olefins.

Authors:  T Pei; R A Widenhoefer
Journal:  J Am Chem Soc       Date:  2001-11-14       Impact factor: 15.419

Review 2.  Asymmetric organocatalysis.

Authors:  Jayasree Seayad; Benjamin List
Journal:  Org Biomol Chem       Date:  2005-02-09       Impact factor: 3.876

3.  Direct catalytic intermolecular alpha-allylic alkylation of aldehydes by combination of transition-metal and organocatalysis.

Authors:  Ismail Ibrahem; Armando Córdova
Journal:  Angew Chem Int Ed Engl       Date:  2006-03-13       Impact factor: 15.336

4.  Total synthesis of celogentin C by stereoselective C-H activation.

Authors:  Yiqing Feng; Gong Chen
Journal:  Angew Chem Int Ed Engl       Date:  2010       Impact factor: 15.336

5.  Combining transition metal catalysis and organocatalysis--an update.

Authors:  Zhenting Du; Zhihui Shao
Journal:  Chem Soc Rev       Date:  2013-02-07       Impact factor: 54.564

6.  Metal-Organic Cooperative Catalysis in C-H and C-C Bond Activation.

Authors:  Dong-Su Kim; Woo-Jin Park; Chul-Ho Jun
Journal:  Chem Rev       Date:  2017-01-06       Impact factor: 60.622

7.  Directed, Regiocontrolled Hydroamination of Unactivated Alkenes via Protodepalladation.

Authors:  John A Gurak; Kin S Yang; Zhen Liu; Keary M Engle
Journal:  J Am Chem Soc       Date:  2016-04-29       Impact factor: 15.419

Review 8.  C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents.

Authors:  Egle M Beccalli; Gianluigi Broggini; Michela Martinelli; Silvia Sottocornola
Journal:  Chem Rev       Date:  2007-11-01       Impact factor: 60.622

9.  Asymmetric organocatalysis combined with metal catalysis: concept, proof of concept, and beyond.

Authors:  Dian-Feng Chen; Zhi-Yong Han; Xiao-Le Zhou; Liu-Zhu Gong
Journal:  Acc Chem Res       Date:  2014-06-09       Impact factor: 22.384

10.  Palladium-catalyzed intramolecular oxidative alkylation of unactivated olefins.

Authors:  Tao Pei; Xiang Wang; Ross A Widenhoefer
Journal:  J Am Chem Soc       Date:  2003-01-22       Impact factor: 15.419

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  5 in total

1.  Mapping Ambiphile Reactivity Trends in the Anti-(Hetero)annulation of Non-Conjugated Alkenes via PdII /PdIV Catalysis.

Authors:  Hui-Qi Ni; Phillippa Cooper; Shouliang Yang; Fen Wang; Neal Sach; Pranali G Bedekar; Joyann S Donaldson; Michelle Tran-Dubé; Indrawan J McAlpine; Keary M Engle
Journal:  Angew Chem Int Ed Engl       Date:  2022-02-02       Impact factor: 15.336

2.  Modular synthesis of non-conjugated N-(quinolin-8-yl) alkenyl amides via cross-metathesis.

Authors:  Hui-Qi Ni; Zi-Qi Li; Van T Tran; Keary M Engle
Journal:  Tetrahedron       Date:  2021-06-12       Impact factor: 2.388

3.  Anti-selective [3+2] (Hetero)annulation of non-conjugated alkenes via directed nucleopalladation.

Authors:  Hui-Qi Ni; Ilia Kevlishvili; Pranali G Bedekar; Joyann S Barber; Shouliang Yang; Michelle Tran-Dubé; Andrew M Romine; Hou-Xiang Lu; Indrawan J McAlpine; Peng Liu; Keary M Engle
Journal:  Nat Commun       Date:  2020-12-22       Impact factor: 14.919

4.  Controlling cyclization pathways in palladium(ii)-catalyzed intramolecular alkene hydro-functionalization via substrate directivity.

Authors:  Xin Wang; Zi-Qi Li; Binh Khanh Mai; John A Gurak; Jessica E Xu; Van T Tran; Hui-Qi Ni; Zhen Liu; Zhonglin Liu; Kin S Yang; Rong Xiang; Peng Liu; Keary M Engle
Journal:  Chem Sci       Date:  2020-09-22       Impact factor: 9.825

Review 5.  Synergistic Strategies in Aminocatalysis.

Authors:  Antonio Del Vecchio; Arianna Sinibaldi; Valeria Nori; Giuliana Giorgianni; Graziano Di Carmine; Fabio Pesciaioli
Journal:  Chemistry       Date:  2022-07-04       Impact factor: 5.020

  5 in total

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