Enantiospecific Synthesis of ortho-Substituted 1,1-Diarylalkanes by a 1,2-Metalate Rearrangement/anti-SN2′ Elimination/Rearomatizing Allylic Suzuki–Miyaura Reaction Sequence

Belén Rubial, Beatrice S.L. Collins, Raphael Bigler, Stefan Aichhorn, Adam Noble, Varinder K. Aggarwal*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

7 Citations (Scopus)
305 Downloads (Pure)

Abstract

The one‐pot sequential coupling of benzylamines, boronic esters and aryl iodides has been investigated. In the presence of an N‐activator, the boronate complex formed from an ortho‐lithiated benzylamine and a boronic ester undergoes stereospecific 1,2‐metalate rearrangement/anti‐SN2' elimination to form a dearomatized tertiary boronic ester. Treatment with an aryl iodide under palladium catalysis leads to rearomatizing γ‐selective allylic Suzuki‐Miyaura cross‐coupling to generate 1,1‐diarylalkanes. When enantioenriched α‐substituted benzylamines are employed, the corresponding 1,1‐diarylalkanes are formed with high stereospecificity.
Original languageEnglish
Pages (from-to)1366-1370
Number of pages5
JournalAngewandte Chemie - International Edition
Volume58
Issue number5
Early online date21 Dec 2018
DOIs
Publication statusPublished - 28 Jan 2019

Keywords

  • 1,1-diarylalkane
  • boronic ester
  • cross-coupling
  • one-pot
  • stereospecific

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