Literature DB >> 24082360

Synthesis of High Oxidation State Molybdenum Imido Heteroatom-Substituted Alkylidene Complexes.

Erik M Townsend1, Stefan M Kilyanek, Richard R Schrock, Peter Müller, Stacey J Smith, Amir H Hoveyda.   

Abstract

Reactions between Mo(class="Chemical">NAr)(class="Chemical">n class="Disease">CHR)(Me2Pyr)-(OTPP) (Ar = 2,6-i-Pr2C6H3, R = H or CHCMe2Ph, Me2Pyr = 2,5-dimethylpyrrolide, OTPP = O-2,3,5,6-Ph4C6H) and CH2=CHX where X = B(pin), SiMe3, N-carbazolyl, N-pyrrolidinonyl, PPh2, OPr, or SPh lead to Mo(NAr)(CHX)-(Me2Pyr)(OTPP) complexes in good yield. All have been characterized through X-ray studies (as an acetonitrile adduct in the case of X = PPh2). The efficiencies of metathesis reactions initiated by Mo(NAr)(CHX)(Me2Pyr)(OTPP) complexes can be rationalized on the basis of steric factors; electronic differences imposed as a consequence of X being bound to the alkylidene carbon do not seem to play a major role. Side reactions that promote catalyst decomposition do not appear to be a serious limitation for Mo=CHX species.

Entities:  

Year:  2013        PMID: 24082360      PMCID: PMC3785106          DOI: 10.1021/om400584f

Source DB:  PubMed          Journal:  Organometallics        ISSN: 0276-7333            Impact factor:   3.876


  15 in total

1.  Highly Selective Ring-Opening/Cross-Metathesis Reactions of Norbornene Derivatives Using Selenocarbene Complexes as Catalysts This work was supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Science, Sports, and Culture, Japan.

Authors:  Hiroyuki Katayama; Hideto Urushima; Tsuneo Nishioka; Chikaya Wada; Masato Nagao; Fumiyuki Ozawa
Journal:  Angew Chem Int Ed Engl       Date:  2000-12-15       Impact factor: 15.336

2.  Enol ethers as substrates for efficient Z- and enantioselective ring-opening/cross-metathesis reactions promoted by stereogenic-at-Mo complexes: utility in chemical synthesis and mechanistic attributes.

Authors:  Miao Yu; Ismail Ibrahem; Masayuki Hasegawa; Richard R Schrock; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2012-01-24       Impact factor: 15.419

3.  Z- and enantioselective ring-opening/cross-metathesis with enol ethers catalyzed by stereogenic-at-Ru carbenes: reactivity, selectivity, and Curtin-Hammett kinetics.

Authors:  R Kashif M Khan; Robert V O'Brien; Sebastian Torker; Bo Li; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2012-07-23       Impact factor: 15.419

4.  Synthesis of molybdenum alkylidene complexes that contain the 2,6-dimesitylphenylimido ligand.

Authors:  Laura C H Gerber; Richard R Schrock; Peter Müller; Michael K Takase
Journal:  J Am Chem Soc       Date:  2011-10-21       Impact factor: 15.419

5.  Efficient and selective formation of macrocyclic disubstituted Z alkenes by ring-closing metathesis (RCM) reactions catalyzed by Mo- or W-based monoaryloxide pyrrolide (MAP) complexes: applications to total syntheses of epilachnene, yuzu lactone, ambrettolide, epothilone C, and nakadomarin A.

Authors:  Chenbo Wang; Miao Yu; Andrew F Kyle; Pavol Jakubec; Darren J Dixon; Richard R Schrock; Amir H Hoveyda
Journal:  Chemistry       Date:  2013-01-23       Impact factor: 5.236

6.  Fundamental studies of tungsten alkylidene imido monoalkoxidepyrrolide complexes.

Authors:  Annie J Jiang; Jeffrey H Simpson; Peter Müller; Richard R Schrock
Journal:  J Am Chem Soc       Date:  2009-06-10       Impact factor: 15.419

7.  Highly regioselective ring-opening/cross-metathesis reactions of 2-sulfonylnorbornene derivatives.

Authors:  G Mahika Weeresakare; Zhuqing Liu; Jon D Rainier
Journal:  Org Lett       Date:  2004-05-13       Impact factor: 6.005

8.  Endo-selective enyne ring-closing metathesis promoted by stereogenic-at-Mo monoalkoxide and monoaryloxide complexes. Efficient synthesis of cyclic dienes not accessible through reactions with Ru carbenes.

Authors:  Yeon-Ju Lee; Richard R Schrock; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2009-08-05       Impact factor: 15.419

9.  Molybdenum-based complexes with two aryloxides and a pentafluoroimido ligand: catalysts for efficient Z-selective synthesis of a macrocyclic trisubstituted alkene by ring-closing metathesis.

Authors:  Chenbo Wang; Fredrik Haeffner; Richard R Schrock; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2013-01-10       Impact factor: 15.336

10.  Catalytic Z-selective olefin cross-metathesis for natural product synthesis.

Authors:  Simon J Meek; Robert V O'Brien; Josep Llaveria; Richard R Schrock; Amir H Hoveyda
Journal:  Nature       Date:  2011-03-24       Impact factor: 49.962

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  8 in total

1.  Catalyst-controlled stereoselective olefin metathesis as a principal strategy in multistep synthesis design: a concise route to (+)-neopeltolide.

Authors:  Miao Yu; Richard R Schrock; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2014-11-06       Impact factor: 15.336

2.  The Versatile Reaction Chemistry of an Alpha-Boryl Diazo Compound.

Authors:  Yao Liu; Raimon Puig de la Bellacasa; Bo Li; Ana Belén Cuenca; Shih-Yuan Liu
Journal:  J Am Chem Soc       Date:  2021-08-25       Impact factor: 16.383

3.  Preparation of macrocyclic Z-enoates and (E,Z)- or (Z,E)-dienoates through catalytic stereoselective ring-closing metathesis.

Authors:  Hanmo Zhang; Elsie C Yu; Sebastian Torker; Richard R Schrock; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2014-11-17       Impact factor: 15.419

4.  Synthesis of Molybdenum and Tungsten Alkylidene Complexes That Contain Sterically Demanding Arenethiolate Ligands.

Authors:  Erik M Townsend; Jakub Hyvl; William P Forrest; Richard R Schrock; Peter Müller; Amir H Hoveyda
Journal:  Organometallics       Date:  2014-09-22       Impact factor: 3.876

5.  Catalytic Z-selective cross-metathesis in complex molecule synthesis: a convergent stereoselective route to disorazole C1.

Authors:  Alexander W H Speed; Tyler J Mann; Robert V O'Brien; Richard R Schrock; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2014-11-07       Impact factor: 15.419

6.  Kinetically E-selective macrocyclic ring-closing metathesis.

Authors:  Xiao Shen; Thach T Nguyen; Ming Joo Koh; Dongmin Xu; Alexander W H Speed; Richard R Schrock; Amir H Hoveyda
Journal:  Nature       Date:  2017-01-09       Impact factor: 49.962

7.  Silyl-Phosphino-Carbene Complexes of Uranium(IV).

Authors:  Erli Lu; Josef T Boronski; Matthew Gregson; Ashley J Wooles; Stephen T Liddle
Journal:  Angew Chem Int Ed Engl       Date:  2018-03-26       Impact factor: 15.336

8.  Direct synthesis of Z-alkenyl halides through catalytic cross-metathesis.

Authors:  Ming Joo Koh; Thach T Nguyen; Hanmo Zhang; Richard R Schrock; Amir H Hoveyda
Journal:  Nature       Date:  2016-03-24       Impact factor: 49.962

  8 in total

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