Nickel-Catalyzed Insertion of Alkynes and Electron-Deficient Olefins into Unactivated sp(3) C-H Bonds

Soham Maity; Soumitra Agasti; Arif Mahammad Earsad; Avijit Hazra; Debabrata Maiti

doi:10.1002/chem.201501962

Nickel-Catalyzed Insertion of Alkynes and Electron-Deficient Olefins into Unactivated sp(3) C-H Bonds

Chemistry. 2015 Aug 3;21(32):11320-4. doi: 10.1002/chem.201501962. Epub 2015 Jun 29.

Authors

Soham Maity¹, Soumitra Agasti¹, Arif Mahammad Earsad¹, Avijit Hazra¹, Debabrata Maiti²

Affiliations

¹ Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai-400076 (India).
² Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai-400076 (India). dmaiti@chem.iitb.ac.in.

PMID: 26121618
DOI: 10.1002/chem.201501962

Abstract

Insertion of unsaturated systems such as alkynes and olefins into unactivated sp(3) C-H bonds remains an unexplored problem. We herein address this issue by successfully incorporating a wide variety of functionalized alkynes and electron-deficient olefins into the unactivated sp(3) C-H bond of pivalic acid derivatives with excellent syn- and linear- selectivity. A strongly chelating 8-aminoquinoline directing group proved beneficial for these insertion reactions, while an air-stable and inexpensive Ni(II) salt has been employed as the active catalyst.

Keywords: alkynes; insertion; nickel; olefins; unactivated sp3.