Prev. Article Next Article Table of Contents

Article

Synthesis and Characterization of R₂PNP(ⁱBuNCH₂CH₂)₃N: A New Bulky Electron-Rich Phosphine for Efficient Pd-Assisted Suzuki−Miyaura Cross-Coupling Reactions

Supporting Info

Jesudoss V. Kingston and John G. Verkade*

Department of Chemistry, Iowa State University, Ames, Iowa 50011

J. Org. Chem., 2007, 72 (8), pp 2816–2822

DOI: 10.1021/jo062452l

Publication Date (Web): March 23, 2007

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

, jverkade@iastate.edu

Abstract

Pro-azaphosphatrane 1a [P(ⁱBuNCH₂CH₂)₃N] reacts with iodine under mild conditions to give [IP(ⁱBuNCH₂CH₂)₃N]I in excellent yield, which on subsequent reaction with ammonia followed by deprotonation with KO^tBu provided HNP(ⁱBuNCH₂CH₂)₃N (3a) in quantitative yield. Reaction of 3a with R‘₂PCl afforded sterically bulky electron-rich phosphines of the type R‘₂PNP(ⁱBuNCH₂CH₂)₃N (4) [R‘ = Ph (4a), ⁱPr (4b), ^tBu (4c)]. The Pd(OAc)₂/4c catalyst system was particularly efficient for the coupling of arylboronic acids with aryl bromides as well as aryl chlorides to give biaryls in excellent yields.

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue April 13, 2007
Received November 29, 2006

Recommend & Share

Related Content

Modified (NHC)Pd(allyl)Cl (NHC = N-Heterocyclic Carbene) Complexes for Room-Temperature Suzuki−Miyaura and Buchwald−Hartwig Reactions Modified (NHC)Pd(allyl)Cl (NHC = N-Heterocyclic Carbene) Complexes for Room-Temperature Suzuki−Miyaura and Buchwald−Hartwig ReactionsJournal of the American Chemical Society
- Modified (NHC)Pd(allyl)Cl (NHC = N-Heterocyclic Carbene) Complexes for Room-Temperature Suzuki−Miyaura and Buchwald−Hartwig Reactions Modified (NHC)Pd(allyl)Cl (NHC = N-Heterocyclic Carbene) Complexes for Room-Temperature Suzuki−Miyaura and Buchwald−Hartwig Reactions
  Nicolas Marion, Oscar Navarro, Jianguo Mei, Edwin D. Stevens, Natalie M. Scott, and Steven P. Nolan
  Journal of the American Chemical Society 2006 128 (12), pp 4101–4111
  Abstract: A series of (NHC)Pd(R-allyl)Cl complexes [NHC: IPr = N,N‘-bis(2,6-diisopropylphenyl)imidazol-2-ylidene, SIPr = N,N‘-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene; R = H, Me, gem-Me₂, Ph] have been synthesized and fully characterized. When ...
  Abstract | Full Text HTML | Hi-Res PDF
Catalysts for Suzuki−Miyaura Coupling Processes: Scope and Studies of the Effect of Ligand StructureJournal of the American Chemical Society
- Catalysts for Suzuki−Miyaura Coupling Processes: Scope and Studies of the Effect of Ligand Structure
  Timothy E. Barder, Shawn D. Walker, Joseph R. Martinelli, and Stephen L. Buchwald
  Journal of the American Chemical Society 2005 127 (13), pp 4685–4696
  Abstract: Suzuki−Miyaura coupling reactions of aryl and heteroaryl halides with aryl-, heteroaryl- and vinylboronic acids proceed in very good to excellent yield with the use of 2-(2‘,6‘-dimethoxybiphenyl)dicyclohexylphosphine, SPhos (1). This ligand confers ...
  Abstract | Full Text HTML | Hi-Res PDF
Versatile Catalysts for the Suzuki Cross-Coupling of Arylboronic Acids with Aryl and Vinyl Halides and Triflates under Mild ConditionsJournal of the American Chemical Society
- Versatile Catalysts for the Suzuki Cross-Coupling of Arylboronic Acids with Aryl and Vinyl Halides and Triflates under Mild Conditions
  Adam F. Littke, Chaoyang Dai, and Gregory C. Fu
  Journal of the American Chemical Society 2000 122 (17), pp 4020–4028
  Abstract: Through the use of Pd₂(dba)₃/P(t-Bu)₃ as a catalyst, a wide range of aryl and vinyl halides, including chlorides, undergo Suzuki cross-coupling with arylboronic acids in very good yield, typically at room temperature; through use of Pd(OAc)₂/PCy₃, a ...
  Abstract | Full Text HTML | Hi-Res PDF

Article

Synthesis and Characterization of R₂PNP(ⁱBuNCH₂CH₂)₃N: A New Bulky Electron-Rich Phosphine for Efficient Pd-Assisted Suzuki−Miyaura Cross-Coupling Reactions