Prev. Article Next Article Table of Contents

Communication

Palladium Pincer Complex Catalyzed Substitution of Vinyl Cyclopropanes, Vinyl Aziridines, and Allyl Acetates with Tetrahydroxydiboron. An Efficient Route to Functionalized Allylboronic Acids and Potassium Trifluoro(allyl)borates

Supporting Info

Sara Sebelius, Vilhelm J. Olsson, and Kálmán J. Szabó*

Department of Organic Chemistry, Stockholm University, SE-106 91 Stockholm, Sweden

J. Am. Chem. Soc., 2005, 127 (30), pp 10478–10479

DOI: 10.1021/ja052885q

Publication Date (Web): July 7, 2005

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, kalman@organ.su.se

Abstract

Palladium-catalyzed boronation of vinyl cyclopropane, vinyl aziridine, and allyl acetate substrates could be accomplished using tetrahydroxydiboron reagent in the presence of SeCSe pincer complex catalyst 1a. These reactions result in allyl boronic acids, which were converted to synthetically useful trifluoro(allyl)borates or allyl boronates. The catalytic transformations proceed under mild and neutral conditions, and therefore many functionalities Br, COOEt, ArSO₂(NH), OAc, and SiRMe₂ are tolerated. The selectivity of the presented processes is very high, affording the linear products incorporating a trans double bond.

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue August 03, 2005
Received May 3, 2005

Recommend & Share

Related Content

Direct Boronation of Allyl Alcohols with Diboronic Acid Using Palladium Pincer-Complex Catalysis. A Remarkably Facile Allylic Displacement of the Hydroxy Group under Mild Reaction ConditionsJournal of the American Chemical Society
- Direct Boronation of Allyl Alcohols with Diboronic Acid Using Palladium Pincer-Complex Catalysis. A Remarkably Facile Allylic Displacement of the Hydroxy Group under Mild Reaction Conditions
  Vilhelm J. Olsson, Sara Sebelius, Nicklas Selander, and Kálmán J. Szabó
  Journal of the American Chemical Society 2006 128 (14), pp 4588–4589
  Abstract: Allyl alcohols were converted to allyl boronic acids and subsequently to trifluoro(allyl)borates with tetrahydroxy diboron using palladium pincer-complex catalysis. These reactions are regio- and stereoselective proceeding with high isolated yields. ...
  Abstract | Full Text HTML | Hi-Res PDF
Stereoselective Construction of Seven-Membered Rings with an All-Carbon Quaternary Center by Direct Tiffeneau−Demjanov-type Ring ExpansionJournal of the American Chemical Society
- Stereoselective Construction of Seven-Membered Rings with an All-Carbon Quaternary Center by Direct Tiffeneau−Demjanov-type Ring Expansion
  Takuya Hashimoto, Yuki Naganawa and Keiji Maruoka
  Journal of the American Chemical Society 2009 131 (18), pp 6614–6617
  Abstract: Insertion of one methylene unit into the C−C bond of cyclohexanones is a potentially useful, straightforward method for the construction of seven-membered carbocycles. An especially appealing but largely unexplored method in this arena is the nucleophilic ...
  Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF
Palladium-Catalyzed Coupling of Allylboronic Acids with Iodobenzenes. Selective Formation of the Branched Allylic Product in the Absence of Directing Groups Palladium-Catalyzed Coupling of Allylboronic Acids with Iodobenzenes. Selective Formation of the Branched Allylic Product in the Absence of Directing GroupsJournal of the American Chemical Society
- Palladium-Catalyzed Coupling of Allylboronic Acids with Iodobenzenes. Selective Formation of the Branched Allylic Product in the Absence of Directing Groups Palladium-Catalyzed Coupling of Allylboronic Acids with Iodobenzenes. Selective Formation of the Branched Allylic Product in the Absence of Directing Groups
  Sara Sebelius, Vilhelm J. Olsson, Olov A. Wallner, and Kálmán J. Szabó
  Journal of the American Chemical Society 2006 128 (25), pp 8150–8151
  Abstract: Palladium-catalyzed coupling reactions of functionalized allylboronic acids with iodobenzenes were achieved under standard Suzuki−Miyaura coupling conditions. The coupling reactions afforded selectively the branched allylic products in high to excellent ...
  Abstract | Full Text HTML | Hi-Res PDF

Communication

Palladium Pincer Complex Catalyzed Substitution of Vinyl Cyclopropanes, Vinyl Aziridines, and Allyl Acetates with Tetrahydroxydiboron. An Efficient Route to Functionalized Allylboronic Acids and Potassium Trifluoro(allyl)borates

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Direct Boronation of Allyl Alcohols with Diboronic Acid Using Palladium Pincer-Complex Catalysis. A Remarkably Facile Allylic Displacement of the Hydroxy Group under Mild Reaction Conditions

Stereoselective Construction of Seven-Membered Rings with an All-Carbon Quaternary Center by Direct Tiffeneau−Demjanov-type Ring Expansion

Other ACS content by these authors:

JOURNALS

BOOKS

MAGAZINE

COMMUNITIES

DIRECTORIES & DATABASES