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2.1.2.1 Aryl- and Hetarylamines with Aryl and Alkenyl Electrophiles

DOI: 10.1055/sos-SD-208-00078

Hay, M. B.; Hicks, J. D.Science of Synthesis: Cross Coupling and Heck-Type Reactions, (20132107.

General Introduction

The N-arylation of aromatic and heteroaromatic amines has developed into a powerful method to construct aromatic amine subunits found in a variety of natural products, pharmaceutical compounds, and materials. The importance of this structural motif has led to the development of numerous robust methods that can effect the arylation of aromatic amines in high yield using a wide array of substrate combinations. Transition-metal-mediated reactions using palladium or copper have rapidly become the preferred method to effect these transformations due to the high tolerance of functional groups and high yields observed using these methods.

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Mee Me(MM)(Me8)MMe eeeeeeeee eeeeeeee eeeeeee eeeeee eeee eee eeeeeeee eeeee eeeeeeeee eeeeeeee e eeeeeeeee eeeee. Mee eeeee eeeeeeeee eeeeeeeee eeeee eee eeeeeeeee(MM) eeeeeeeee eeeeeeee eeeeeee eee ee eeee eeeeeeeeeeee.[‌88‌] Mee eeeeeee eeeeeeee eee eeeeeeeeeeeeee eeeee eeeeeeeeeeee, eee eeeeeee eeeeeee ee eeeee eee eeee-eeeeeeee eeee ee eee eeeeeeeee eeeee.[‌88‌] Meeeeee ee eeeee eeee eeeeeeeeeeeeeee, eeeeeeee-eeee eeeeeeee eeeee eeeeeeeeee eee eeeeeeeee eeee eeeeeeeeee eee M—M eeeee eeeeeeee.[‌88‌] Meeeeeeeee, eeeeeeee-eeeeeeeee eeeeeee eeeeeeeeeee eee eeeeeeeee eeeeeeeeeee eeeeeeeeee eee ee eeeee eeeeeee eeeeeeeeeeeeeee eee eeeeee eeeeeee ee eeeeeeeeee ee eee Me(MM)(Me8)MMe eeeeeeeee eeeeeeee eeeeeee.[‌88‌,‌88‌] Mee eeeeeeeeeeeee eeeee ee eeeeeeeeeee ee eee eeeeeeeee eeeeeee ee eee eeeeeeeee M—M eeee eeee eeeeeee ee eee eeeeeeeee eeeeeeee eeeeeee.[‌88‌] Mee eeeeeeeee eeeeeee ee eeee eeee eeeeeee ee e eeeeeee ee eeeeee ee eeee eeeee eeeee eeee ee eeeeeeeeeee eeee eeeeeee.[‌88‌] Me e eeeeee, e eeee eeeee ee eeeee eeee eeee eeeeeeee ee eeeee eeeeeeeee, eeeeeeeee eeeeee eeeee eeee-eeeeeeeee, eeeeeee eeeeeeeeeeeeeeeeeeeeee, eeeeeeeee eeeeeeeee, eeeeeeeee eeeeeeeee, ee eeeeee eeeeeeeee. Meeeee eeeee eeeeeee eeeeeeeee eeeeeeeeeeeee eeeee, eee eee eee ee eeeeeeeeee eeee eeee-eeeeeeeee eeeeeeeeee eeeeee. Me eeeee eeeee, eeeeee eeeee eeee ee eeeeeeeee eeeeeeeee, eeeeeeeee eeeeeeeee, ee eeeeee eeeeeeeee eee ee eeeeeeee.

Mee eeeee eeee ee eee eeeeeeeee eeeee, M—M eeee-eeeeeee eeeeeeeee eeeeeeeeeee, ee eeeee eeeeeeeeeee ee eeeee, eeeeeeeeee eeeeeeeeee eeeeeeeeeee eeeeeee [e.e., eee-eeee-eeeeeeeeeeeeee ee eeeeeee(eeeeee)eeeeeeeeee] ee eeeee-eeee-eeeee eeeeeeeee eeeeeee [e.e., MMMMM, Meeeeeee, ee MeMM-eMe (eee Meeeee 8)].[‌88‌] Me eeeeeeee ee eeeeeeeee eeeeeeee, eeeeeeeee eeeeeeeeee eeeeeeee-eeee eeeeeeeee eeeeeee eeeeeee M—M eeee-eeeeeee eeeeeeeee eeeeeeeeeee.[‌88‌]

Meeeeeeeeeee Meeeeeeeeeeeee eee Meeeeeeee-Meeeeeeee M-Meeeeeeee: Mee eeeeeeeeee eeeeeeeee ee eeeeeeeee-eeeeeeeee eeeeeeee eee eeeeeeeeeeeeee eeeee eeeeeeeee eeeeeeeee eeeeeeee eeeeeeeeeeeee ee eeeeeee eeeeeeeeeeee eeeeeeeee, eeeeeeeee eeeeee eeeeeeeee, eeeee eeeeeeeeeee, eee eeee eeeeeeee eeee.[‌88‌]

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Meeee 8 Meeeeeeeee eee Meeeeeeeeee ee Meeeee-Meeeeeeee M-Meeeeeeee ee Meeeeeee Meeeee[‌88‌-‌88‌]

Meeeeeeeee ee Me Meeeeeeeeee ee Me
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Meeeeeeeeeee Meeeeeeeeeeeee eee Meeeee-Meeeeeeee M-Meeeeeeee: Meeeee-eeeeeeeee eeeeeeeeee eeeeeee eeeeeee eeeeeeeeeeee eeeeeeeeeee ee eeeee eeeeeeeee eeeeeeeeeeee. Mee eeeeeee, eeeeee-eeeeeeeee eeeeeeeeee eee eeeeeeeee eee eeeee e eeeeeeee ee eeeee eeeeeeeeee ee eee eeeeeee ee eeeee. Me eeeeeeeeee, eeeeee-eeeeeeee eeeeeeeee eeee eeeeeeeee eeeeeeeeeee ee eeeee.[‌88‌] Meeeeeeeee eeeee eee eeeeee ee eeeeeeeeeeee eeeeeeeeee ee eee eeee eeeeee eeee eeeeee eee eeeeee eeeee eeee eeeeeeee.[‌88‌] Me eeeee eee eeeeeeeee-eeeeeeeee eeeeeeeeee, eee eee ee eeeeeeeee eeeeeeeee eeeee eee eeee ee eeeeeeee eeeeeeeeeee. Meeeeeeee, ee ee eeeeeeeeeee ee eeee eeeee eeeee eeeee ee eee ee eeeee ee eeeeee eeeeeeeeeeee eeeeeee.

Meeeee-Meeeeeee Meeeeeeee M—M Meeeeeee: Mee eeeeeeeee eeeeeeee ee eeeeee eeee eeeeeeeeeee eeeee eeeeeeeee ee Meee eee Mee eee eeeeee e eeeeeeeeeeeee eeeeeeeeeee ee eeeeeee M-eeeeeeeee eeeeeeeee eee eee eeeeeeeee ee eeeeeeee eeeeee.[‌88‌,‌88‌] Mee eeeeeeee eeeeeee eee eeeeeeeee M—M eeeeeeee eeeeeee eeeeeeeeeeeeee eeeeee, eee eeee eeeeee eeeeeeeeeeee eeee eeeeeeee eee eeeeeeee eeeeeeeee eeeeeee eee eee ee eeeeee ee e eeeeeeee eeeeeee.[‌88‌,‌88‌]

Meee–Mee–Meeee eeeeeeeee eeee eeee eeeeeeeeee eeee eeeeeeee eeee eeeeeeeeeee eeeeee- eee eeeeeeeee-eeeeeeee eeeee eeeeeeeee. Meeeee-eeeeeeee eeeeeeeee eeeeeeee eeeeeeeee eee eeeee eeeeeeee eeeee eeee eeeeeeee eeeeeeeeee (e.e., eeee eeeeeeeeeee eeee ee eeeee eeee), eeeee eee ee eeeeeeeee eee eeeeeeeee eeeeeeeeee. Meeeeeeeeeee, eeeee eeeeeeeee eee eeeee eeeeeeee ee e eeee eeeee ee eeeeeeeeeeee. Mee eeeeeeeeeee ee eeee eeeeee eee eeeeeee ee eeeee ee eeeeee-eeeeeeee eeeeeeeeee eeeee eeee eeeeeee. Mee eeeeeee, eeeee eeeeeeeee eee eeeeeeeee ee eeeeee eeeeeeeeeeeeee, ee eeeeeeeee eeeeeeee eeeeee eee 8-eeeeeeeeeee eeeeeeeeeee eeeee eee eeeee eeeeeeeeeee eeeeeeeee eeeeeeeeeeee.[‌88‌]

Meee ee eeeeeeeeeeee eeeeeeeeee, eeeeee-eeeeeeee eeeeeeeee eeeee eeeeeeeee eeee eeeeeee eeeeeeeeeee. Meeee eeeeeeeee eee eeeee eee eeeee ee eeeeeee eeeeeeeeee, ee eeeeee ee eeeeeeee eeee ee e eeeeeeee eeeeeee. Me eeee eeeee, eeeee eeeeeeeee eee ee eeeeeeee eeeeeeeee eee eeeeeeeee eeeeee eee eeeee ee eeeeeeee eeeee, eeeeeeeeee eeeeeeeee eeeeeeeeee ee eee eeeeeee eeee eeee eee eeeeeeeeeeeee eeeeee. Meeee, eeeeeeeee eeeeeeee eeeee eee eeeeeeee eeeeeeeeeeeeeee eee ee eeeeeeee eeeeeee eee eeeeeeee ee e eeeeee-eeeeeeeeeeee eeeee. Meee-eeeee eeeeeeeeee eeeee, eeee ee eeeeeeeeeeeee eeee (eeeeeeee eeee), eee eeeee eeeeeeee eee eeee eeeeeee.[‌88‌]

References