Arylation of Azaarylmethylamines with Aryl Chlorides and a NiBr2/NIXANTPHOS-based Catalyst

Gui Gao; Yue Fu; Minyan Li; Bo Wang; Bing Zheng; Shicong Hou; Patrick J Walsh

doi:10.1002/adsc.201700438

Arylation of Azaarylmethylamines with Aryl Chlorides and a NiBr₂/NIXANTPHOS-based Catalyst

Adv Synth Catal. 2017 Aug 17;359(16):2890-2894. doi: 10.1002/adsc.201700438. Epub 2017 Jul 12.

Authors

Gui Gao¹, Yue Fu², Minyan Li², Bo Wang¹, Bing Zheng¹, Shicong Hou¹, Patrick J Walsh²

Affiliations

¹ Department of Applied Chemistry, China Agricultural University, Beijing 100193, P. R. China.
² Roy and Diana Vagelos Laboratories, Penn/Merck Laboratory for High-Throughput Experimentation, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States.

Abstract

A nickel-catalyzed coupling of azaarylmethylamines with aryl chlorides has been achieved. NIXANTPHOS together with low cost NiBr₂ was successfully developed and optimized to exhibit high reactivity at 2.5 mol % loading. Under optimized reaction conditions, aryl(azaaryl)methylamine products were afforded in good to excellent yields (22 examples, up to 98% yield).

Keywords: Aryl Chlorides; Arylation; Azaarylmethylamines; NIXANTPHOS; NiBr2.

Grants and funding

R01 GM104349/GM/NIGMS NIH HHS/United States