Literature DB >> 25715077

An efficient method for the preparation of styrene derivatives via Rh(III)-catalyzed direct C-H vinylation.

Kate D Otley1, Jonathan A Ellman.   

Abstract

The development of a method for the Rh(III)-catalyzed direct vinylation of an aromatic C-H bond to give functionalized styrenes in good yield, using vinyl acetate as a convenient and inexpensive vinyl source, is reported. High functional group tolerance is demonstrated for electronically distinct arenes as well as different directing groups. Mechanistic investigation resulted in the characterization of a novel rhodium-metallacycle, which represents the first X-ray structure of a [1,2]-Rh(III)-alkenyl addition adduct.

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Year:  2015        PMID： 25715077      PMCID： PMC4446975          DOI： 10.1021/acs.orglett.5b00340

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


  24 in total

1.  The asymmetric intramolecular Heck reaction in natural product total synthesis.

Authors:  Amy B Dounay; Larry E Overman
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

2.  The Ru(cod)(cot)-catalyzed alkenylation of aromatic C-H bonds with alkenyl acetates.

Authors:  Yusuke Matsuura; Masaru Tamura; Takuya Kochi; Mitsuo Sato; Naoto Chatani; Fumitoshi Kakiuchi
Journal:  J Am Chem Soc       Date:  2007-07-25       Impact factor: 15.419

3.  Oxidative coupling of aromatic substrates with alkynes and alkenes under rhodium catalysis.

Authors:  Tetsuya Satoh; Masahiro Miura
Journal:  Chemistry       Date:  2010-10-04       Impact factor: 5.236

4.  Rhodium(iii)-catalyzed C-H allylation of electron-deficient alkenes with allyl acetates.

Authors:  Chao Feng; Daming Feng; Teck-Peng Loh
Journal:  Chem Commun (Camb)       Date:  2014-11-14       Impact factor: 6.222

5.  Mild Rh(III)-catalyzed C7-allylation of indolines with allylic carbonates.

Authors:  Jihye Park; Neeraj Kumar Mishra; Satyasheel Sharma; Sangil Han; Youngmi Shin; Taejoo Jeong; Joa Sub Oh; Jong Hwan Kwak; Young Hoon Jung; In Su Kim
Journal:  J Org Chem       Date:  2015-01-20       Impact factor: 4.354

6.  Rh(III)-Catalyzed Oxidative Coupling of Benzoic Acids with Geminal-Substituted Vinyl Acetates: Synthesis of 3-Substituted Isocoumarins.

Authors:  Mingliang Zhang; Hui-Jun Zhang; Tiantian Han; Wenqing Ruan; Ting-Bin Wen
Journal:  J Org Chem       Date:  2014-12-01       Impact factor: 4.354

7.  Synthesis of styrenes by palladium(II)-catalyzed vinylation of arylboronic acids and aryltrifluoroborates by using vinyl acetate.

Authors:  Jonas Lindh; Jonas Sävmarker; Peter Nilsson; Per J R Sjöberg; Mats Larhed
Journal:  Chemistry       Date:  2009       Impact factor: 5.236

8.  Oxidant-free Rh(III)-catalyzed direct C-H olefination of arenes with allyl acetates.

Authors:  Chao Feng; Daming Feng; Teck-Peng Loh
Journal:  Org Lett       Date:  2013-07-01       Impact factor: 6.005

9.  Vinylation of aromatic halides using inexpensive organosilicon reagents. Illustration of design of experiment protocols.

Authors:  Scott E Denmark; Christopher R Butler
Journal:  J Am Chem Soc       Date:  2008-02-28       Impact factor: 15.419

Review 10.  Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions: versatility and practicality.

Authors:  Xiao Chen; Keary M Engle; Dong-Hui Wang; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336
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  3 in total

1.  Rh(III)-Catalyzed Aryl and Alkenyl C-H Bond Addition to Diverse Nitroalkenes.

Authors:  Tyler J Potter; David N Kamber; Brandon Q Mercado; Jonathan A Ellman
Journal:  ACS Catal       Date:  2016-12-02       Impact factor: 13.084

2.  Convergent Synthesis of Diverse Nitrogen Heterocycles via Rh(III)-Catalyzed C-H Conjugate Addition/Cyclization Reactions.

Authors:  Adam B Weinstein; Jonathan A Ellman
Journal:  Org Lett       Date:  2016-06-23       Impact factor: 6.005

3.  Highly Efficient Gold(I)-Catalyzed Regio- and Stereoselective Hydrocarboxylation of Internal Alkynes.

Authors:  Stéphanie Dupuy; Danila Gasperini; Steven P Nolan
Journal:  ACS Catal       Date:  2015-10-12       Impact factor: 13.084
  3 in total

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