Prev. Article Next Article Table of Contents

Letter

First Catalytic and Green Synthesis of Aryl-(Z)-vinyl Chlorides and Its Plausible Addition−Elimination Mechanism

Supporting Info

Weike Su* and Can Jin

College of Pharmaceutical Sciences, Zhejiang University of Technology, Zhejiang Key Laboratory of Pharmaceutical Engineering, Hangzhou 310014, PRC

Org. Lett., 2007, 9 (6), pp 993–996

DOI: 10.1021/ol062991c

Publication Date (Web): February 23, 2007

To whom correspondence should be addressed. Fax: (+86)571-88320752.

, suweike@zjut.edu.cn

Abstract

Via a catalytic cycle in the presence of scandium triflate (2 mol %)/DMF (1 mol %)/benzoyl chloride (5 mol %), aromatic ketones were treated with bis(trichloromethyl) carbonate (BTC) to afford aryl-(Z)-vinyl chlorides. All metal triflates tested in the reaction showed highly catalytic activity. A plausible addition−elimination mechanism was proposed. The present work describes the first catalytic and green route to the synthesis of aryl-(Z)-vinyl chlorides.

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue March 15, 2007
Received December 11, 2006

Recommend & Share

Related Content

Enantiospecific Total Synthesis of the Hapalindoles, Fischerindoles, and Welwitindolinones via a Redox Economic ApproachJournal of the American Chemical Society
- Enantiospecific Total Synthesis of the Hapalindoles, Fischerindoles, and Welwitindolinones via a Redox Economic Approach
  Jeremy M. Richter, Yoshihiro Ishihara, Takeshi Masuda, Brandon W. Whitefield, Toms Llamas, Antti Pohjakallio and Phil S. Baran
  Journal of the American Chemical Society 2008 130 (52), pp 17938–17954
  Abstract: Full details are provided for the total synthesis of several members of the hapalindole family of natural products, including hapalindole Q, 12-epi-hapalindole D, 12-epi-fischerindole U, 12-epi-fischerindole G, 12-epi-fischerindole I, and welwitindolinone ...
  Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF
A Concise Total Synthesis of (−)-Quinocarcin via Aryne AnnulationJournal of the American Chemical Society
- A Concise Total Synthesis of (−)-Quinocarcin via Aryne Annulation
  Kevin M. Allan and Brian M. Stoltz
  Journal of the American Chemical Society 2008 130 (51), pp 17270–17271
  Abstract: Described in this report is a rapid asymmetric total synthesis of the tetrahydroisoquinoline antitumor antibiotic (−)-quinocarcin. The sequence employs a mild fluoride-induced aryne annulation developed in our laboratories to build a key isoquinoline-...
  Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF
A Mild Synthesis of Vinyl Halides and gem-Dihalides Using Triphenyl Phosphite−Halogen-Based ReagentsThe Journal of Organic Chemistry
- A Mild Synthesis of Vinyl Halides and gem-Dihalides Using Triphenyl Phosphite−Halogen-Based Reagents
  Alberto Spaggiari, Daniele Vaccari, Paolo Davoli, Giovanni Torre, and Fabio Prati
  The Journal of Organic Chemistry 2007 72 (6), pp 2216–2219
  Abstract: A new application of (PhO)₃P−halogen-based reagents to the synthesis of vinyl halides and gem-dihalides is described. Vinyl halides were prepared in good to excellent yields from enolizable ketones, whereas aldehydes afforded the corresponding gem-...
  Abstract | Full Text HTML | Hi-Res PDF

Letter

First Catalytic and Green Synthesis of Aryl-(Z)-vinyl Chlorides and Its Plausible Addition−Elimination Mechanism

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Enantiospecific Total Synthesis of the Hapalindoles, Fischerindoles, and Welwitindolinones via a Redox Economic Approach

A Concise Total Synthesis of (−)-Quinocarcin via Aryne Annulation

A Mild Synthesis of Vinyl Halides and gem-Dihalides Using Triphenyl Phosphite−Halogen-Based Reagents

Other ACS content by these authors:

JOURNALS

BOOKS

MAGAZINE

COMMUNITIES

DIRECTORIES & DATABASES