Nickel(0)-catalyzed [2 + 2 + 1] carbonylative cycloaddition of imines and alkynes or norbornene leading to γ-lactams

Yoichi Hoshimoto; Tomoya Ohata; Yukari Sasaoka; Masato Ohashi; Sensuke Ogoshi

doi:10.1021/ja509171a

Nickel(0)-catalyzed [2 + 2 + 1] carbonylative cycloaddition of imines and alkynes or norbornene leading to γ-lactams

J Am Chem Soc. 2014 Nov 12;136(45):15877-80. doi: 10.1021/ja509171a. Epub 2014 Nov 4.

Authors

Yoichi Hoshimoto¹, Tomoya Ohata, Yukari Sasaoka, Masato Ohashi, Sensuke Ogoshi

Affiliation

¹ Department of Applied Chemistry, Faculty of Engineering, Osaka University , Suita, Osaka 565-0871, Japan.

PMID: 25354361
DOI: 10.1021/ja509171a

Abstract

The first nickel(0)-catalyzed [2 + 2 + 1] carbonylative cycloaddition reaction of imines and alkynes or norbornene has been achieved by employing phenyl formate as a CO source. With this method, a variety of N-benzenesulfonyl, -tosyl, and -phosphoryl-substituted γ-lactams can be prepared in good to high yields.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkynes / chemistry*
Catalysis
Cycloaddition Reaction
Imines / chemistry*
Models, Molecular
Molecular Conformation
Nickel / chemistry*
Norbornanes / chemistry*

Substances

Alkynes
Imines
Norbornanes
2-norbornene
Nickel