Carbopalladation of C–C σ-bonds enabled by strained boronate complexes

Alexander Fawcett, Tobias Biberger, Varinder K. Aggarwal*

*Corresponding author for this work

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

40 Citations (Scopus)
331 Downloads (Pure)

Abstract

Transition-metal-catalysed cross-coupling reactions, particularly those mediated by palladium, are some of the most broadly used chemical transformations. The fundamental reaction steps of such cross-couplings typically include oxidative addition, transmetallation, carbopalladation of a π-bond and/or reductive elimination. Herein, we describe an unprecedented fundamental reaction step: a C–C σ-bond carbopalladation. Specifically, an aryl palladium(ii) complex interacts with a σ-bond of a strained bicyclo[1.1.0]butyl boronate complex to enable addition of the aryl palladium(ii) species and an organoboronic ester substituent across a C–C σ-bond. The overall process couples readily available aryl triflates and organoboronic esters across a cyclobutane unit with total diastereocontrol. The pharmaceutically relevant 1,1,3-trisubstituted cyclobutane products are decorated with an array of modular building blocks, including a boronic ester that can be readily derivatized.

Original languageEnglish
Pages (from-to)117-122
Number of pages6
JournalNature Chemistry
Volume11
Issue number2
Early online date10 Dec 2018
DOIs
Publication statusPublished - Feb 2019

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