Literature DB >> 24736839

Catalytic bismetallative multicomponent coupling reactions: scope, applications, and mechanisms.

Hee Yeon Cho1, James P Morken.   

Abstract

Catalytic reactions have played an indispensable role in organic chemistry for the last several decades. In particular, catalytic multicomponent reactions have attracted significant attention due to their efficiency and expediency towards complex molecule synthesis. The presence of bismetallic reagents (e.g. B-B, Si-Si, B-Si, Si-Sn, etc.) in this process renders the products enriched with various functional groups and multiple stereocenters. For this reason, catalytic bismetallative coupling is considered an effective method to generate the functional and stereochemical complexity of simple hydrocarbon substrates. This review highlights key developments of transition-metal catalyzed bismetallative reactions involving multiple π components. Specifically, it will highlight the scope, synthetic applications, and proposed mechanistic pathways of this process.

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Year:  2014        PMID: 24736839      PMCID: PMC4100251          DOI: 10.1039/c3cs60482a

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


  13 in total

1.  Recent developments in asymmetric multicomponent reactions.

Authors:  Corien de Graaff; Eelco Ruijter; Romano V A Orru
Journal:  Chem Soc Rev       Date:  2012-05-21       Impact factor: 54.564

2.  A highly stereoselective sequential allylic transfer reaction of diene with diboronyl reagent and aldehydes promoted by nickel catalyst.

Authors:  Chan-Mo Yu; Jinsuop Youn; Seok-Keun Yoon; Young-Tack Hong
Journal:  Org Lett       Date:  2005-09-29       Impact factor: 6.005

3.  Reversible carbon-carbon bond formation between 1,3-dienes and aldehyde or ketone on nickel(0).

Authors:  Sensuke Ogoshi; Kei-ichi Tonomori; Masa-aki Oka; Hideo Kurosawa
Journal:  J Am Chem Soc       Date:  2006-05-31       Impact factor: 15.419

4.  Nickel-catalyzed enantio- and diastereoselective three-component coupling of 1,3-dienes, aldehydes, and a silylborane leading to α-chiral allylsilanes.

Authors:  Nozomi Saito; Ayami Kobayashi; Yoshihiro Sato
Journal:  Angew Chem Int Ed Engl       Date:  2011-12-15       Impact factor: 15.336

5.  Diastereoselective construction of functionalized homoallylic alcohols by Ni-catalyzed diboron-promoted coupling of dienes and aldehydes.

Authors:  Hee Yeon Cho; James P Morken
Journal:  J Am Chem Soc       Date:  2008-12-03       Impact factor: 15.419

6.  Platinum-catalyzed tandem diboration/asymmetric allylboration: access to nonracemic functionalized 1,3-diols.

Authors:  Jeremy B Morgan; James P Morken
Journal:  Org Lett       Date:  2003-07-10       Impact factor: 6.005

Review 7.  Nickel-catalyzed reductive cyclizations and couplings.

Authors:  John Montgomery
Journal:  Angew Chem Int Ed Engl       Date:  2004-07-26       Impact factor: 15.336

Review 8.  Catalytic enantioselective diboration, disilation and silaboration: new opportunities for asymmetric synthesis.

Authors:  Heather E Burks; James P Morken
Journal:  Chem Commun (Camb)       Date:  2007-08-22       Impact factor: 6.222

9.  Mechanism and transition-state structures for nickel-catalyzed reductive alkyne-aldehyde coupling reactions.

Authors:  P R McCarren; Peng Liu; Paul Ha-Yeon Cheong; Timothy F Jamison; K N Houk
Journal:  J Am Chem Soc       Date:  2009-05-20       Impact factor: 15.419

10.  Palladium-catalyzed regio- and diastereoselective tandem silastannylation/allyl addition of allene aldehydes and allene ketones: synthesis of cis cyclopentanols and cyclohexanols.

Authors:  Suk-Ku Kang; Young-Hwan Ha; Byung-Soo Ko; Yoongho Lim; Jihyun Jung
Journal:  Angew Chem Int Ed Engl       Date:  2002-01-18       Impact factor: 15.336

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  11 in total

1.  Copper-Catalyzed 1,2-Amino Oxygenation of 1,3-Dienes: A Chemo-, Regio-, and Site-Selective Three-Component Reaction with O-Acylhydroxylamines and Carboxylic Acids.

Authors:  Brett N Hemric; Andy W Chen; Qiu Wang
Journal:  ACS Catal       Date:  2019-09-24       Impact factor: 13.084

2.  Regioselective Arylboration of Isoprene and Its Derivatives by Pd/Cu Cooperative Catalysis.

Authors:  Kevin B Smith; M Kevin Brown
Journal:  J Am Chem Soc       Date:  2017-06-05       Impact factor: 15.419

3.  Employing of Fe3O4/CuO/ZnO@MWCNT MNCs in the solvent-free synthesis of new cyanopyrroloazepine derivatives and investigation of biological activity.

Authors:  Neda Zare Davijani; Reza Kia-Kojoori; Shahrzad Abdolmohammadi; Sepehr Sadegh-Samiei
Journal:  Mol Divers       Date:  2021-12-03       Impact factor: 3.364

Review 4.  Intermolecular Metal-Catalyzed Reductive Coupling of Dienes, Allenes, and Enynes with Carbonyl Compounds and Imines.

Authors:  Michael Holmes; Leyah A Schwartz; Michael J Krische
Journal:  Chem Rev       Date:  2018-06-13       Impact factor: 60.622

5.  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

6.  Enantioselective Generation of Adjacent Stereocenters in a Copper-Catalyzed Three-Component Coupling of Imines, Allenes, and Diboranes.

Authors:  Kay Yeung; Rebecca E Ruscoe; James Rae; Alexander P Pulis; David J Procter
Journal:  Angew Chem Int Ed Engl       Date:  2016-08-19       Impact factor: 15.336

Review 7.  Mechanochemical synthesis of small organic molecules.

Authors:  Tapas Kumar Achar; Anima Bose; Prasenjit Mal
Journal:  Beilstein J Org Chem       Date:  2017-09-11       Impact factor: 2.883

8.  Bran-New Four-Molecule and Five-Molecule Cascade Reactions for One-Pot Synthesis of Pyrano[3,2-c]chromen-5-ones and Spiro[benzo[b][1,4]diazepine-2,2'-pyrano[3,2-c]chromen]-5'-ones under Catalyst- and Solvent-Free Conditions.

Authors:  Guoxun Zhu; Zhou Yi; Jie Zhou; Zhiyong Chen; Pengran Guo; Yanying Huang; Jianghan Chen; Huacan Song; Wei Yi
Journal:  ACS Omega       Date:  2018-10-18

9.  Ligand-controlled diastereodivergent, enantio- and regioselective copper-catalyzed hydroxyalkylboration of 1,3-dienes with ketones.

Authors:  Jian-Jun Feng; Yan Xu; Martin Oestreich
Journal:  Chem Sci       Date:  2019-08-20       Impact factor: 9.825

10.  Design and synthesis of magnetic Fe3O4@NFC-ImSalophCu nanocatalyst based on cellulose nanofibers as a new and highly efficient, reusable, stable and green catalyst for the synthesis of 1,2,3-triazoles.

Authors:  Pouya Ghamari Kargar; Ghodsieh Bagherzade; Hossein Eshghi
Journal:  RSC Adv       Date:  2020-09-04       Impact factor: 3.361

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