Literature DB >> 27505233

Manganese-Catalyzed Carboacylations of Alkenes with Alkyl Iodides.

Caitlin M McMahon1, Matthew S Renn1, Erik J Alexanian1.   

Abstract

A manganese-catalyzed carboacylation of alkenes with alkyl iodides and carbon monoxide is described. This carbonylative difunctionalization uses both primary and secondary alkyl iodides in reactions with a diverse array of cyclic and acyclic substrates. Examples of successful applications to the synthesis of five-, six-, and seven-membered rings are provided. The inexpensive, first-row catalytic system and mild reaction conditions are expected to facilitate applications in complex synthesis.

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Year:  2016        PMID: 27505233      PMCID: PMC5359471          DOI: 10.1021/acs.orglett.6b02154

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  19 in total

1.  Catalysts for cross-coupling reactions with non-activated alkyl halides.

Authors:  Anja C Frisch; Matthias Beller
Journal:  Angew Chem Int Ed Engl       Date:  2005-01-21       Impact factor: 15.336

Review 2.  Secondary alkyl halides in transition-metal-catalyzed cross-coupling reactions.

Authors:  Alena Rudolph; Mark Lautens
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

3.  Palladium-catalyzed Heck-type cross-couplings of unactivated alkyl iodides.

Authors:  Caitlin M McMahon; Erik J Alexanian
Journal:  Angew Chem Int Ed Engl       Date:  2014-04-23       Impact factor: 15.336

4.  Palladium-catalyzed, ring-forming aromatic C-H alkylations with unactivated alkyl halides.

Authors:  Alexander R O Venning; Patrick T Bohan; Erik J Alexanian
Journal:  J Am Chem Soc       Date:  2015-03-16       Impact factor: 15.419

5.  Cobalt-catalyzed trimethylsilylmethylmagnesium-promoted radical alkenylation of alkyl halides: a complement to the Heck reaction.

Authors:  Walter Affo; Hirohisa Ohmiya; Takuma Fujioka; Yousuke Ikeda; Tomoaki Nakamura; Hideki Yorimitsu; Koichiro Oshima; Yuki Imamura; Tsutomu Mizuta; Katsuhiko Miyoshi
Journal:  J Am Chem Soc       Date:  2006-06-21       Impact factor: 15.419

6.  Pd-catalyzed cross-coupling reactions of alkyl halides.

Authors:  Nobuaki Kambe; Takanori Iwasaki; Jun Terao
Journal:  Chem Soc Rev       Date:  2011-07-25       Impact factor: 54.564

7.  Palladium-catalyzed carbonylative Heck-type reactions of alkyl iodides.

Authors:  Kayla S Bloome; Erik J Alexanian
Journal:  J Am Chem Soc       Date:  2010-09-22       Impact factor: 15.419

8.  Palladium-catalyzed Heck-type reactions of alkyl iodides.

Authors:  Kayla S Bloome; Rebecca L McMahen; Erik J Alexanian
Journal:  J Am Chem Soc       Date:  2011-11-23       Impact factor: 15.419

9.  Palladium-catalyzed carbonylation reactions of aryl halides and related compounds.

Authors:  Anne Brennführer; Helfried Neumann; Matthias Beller
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

10.  Endo-selective Pd-catalyzed silyl methyl Heck reaction.

Authors:  Marvin Parasram; Viktor O Iaroshenko; Vladimir Gevorgyan
Journal:  J Am Chem Soc       Date:  2014-12-17       Impact factor: 15.419

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  9 in total

1.  Manganese-catalysed divergent silylation of alkenes.

Authors:  Jie Dong; Xiang-Ai Yuan; Zhongfei Yan; Liying Mu; Junyang Ma; Chengjian Zhu; Jin Xie
Journal:  Nat Chem       Date:  2020-12-14       Impact factor: 24.427

2.  Transition-Metal (Pd, Ni, Mn)-Catalyzed C-C Bond Constructions Involving Unactivated Alkyl Halides and Fundamental Synthetic Building Blocks.

Authors:  Megan R Kwiatkowski; Erik J Alexanian
Journal:  Acc Chem Res       Date:  2019-03-25       Impact factor: 22.384

3.  Cross-Selective Aza-Pinacol Coupling via Atom Transfer Catalysis.

Authors:  Sean M Rafferty; Joy E Rutherford; Lumin Zhang; Lu Wang; David A Nagib
Journal:  J Am Chem Soc       Date:  2021-04-08       Impact factor: 15.419

4.  Ni(I)-Catalyzed β,δ-Vinylarylation of γ,δ-Alkenyl α-Cyanocarboxylic Esters via Contraction of Transient Nickellacycles.

Authors:  Roshan K Dhungana; Shekhar Kc; Prakash Basnet; Vivek Aryal; Lucas J Chesley; Ramesh Giri
Journal:  ACS Catal       Date:  2019-10-29       Impact factor: 13.700

5.  Transition Metal (Ni, Cu, Pd)-Catalyzed Alkene Dicarbofunctionalization Reactions.

Authors:  Laura M Wickham; Ramesh Giri
Journal:  Acc Chem Res       Date:  2021-08-12       Impact factor: 24.466

6.  Ni-catalysed regioselective 1,2-diarylation of unactivated olefins by stabilizing Heck intermediates as pyridylsilyl-coordinated transient metallacycles.

Authors:  Surendra Thapa; Roshan K Dhungana; Rajani Thapa Magar; Bijay Shrestha; Shekhar Kc; Ramesh Giri
Journal:  Chem Sci       Date:  2017-11-27       Impact factor: 9.825

7.  Intermolecular selective carboacylation of alkenes via nickel-catalyzed reductive radical relay.

Authors:  Xian Zhao; Hai-Yong Tu; Lei Guo; Shengqing Zhu; Feng-Ling Qing; Lingling Chu
Journal:  Nat Commun       Date:  2018-08-28       Impact factor: 14.919

8.  Synthesis of unprotected glyco-alkynones via molybdenum-catalyzed carbonylative Sonogashira cross-coupling reaction.

Authors:  Mariana P Darbem; Henrique A Esteves; Robert A Burrow; Antônio A Soares-Paulino; Daniel C Pimenta; Hélio A Stefani
Journal:  RSC Adv       Date:  2022-01-13       Impact factor: 3.361

9.  Cu/Mn bimetallic catalysis enables carbonylative Suzuki-Miyaura coupling with unactivated alkyl electrophiles.

Authors:  Dominic R Pye; Li-Jie Cheng; Neal P Mankad
Journal:  Chem Sci       Date:  2017-03-31       Impact factor: 9.825

  9 in total

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