Science of Synthesis

Tomás-Gamasa, M., Science of Synthesis: Cross Coupling and Heck-Type Reactions, (2013) 2, 23.

The discovery of the copper-promoted Chan–Lam–Evans coupling reaction[‌51‌,‌52‌] in 1998 greatly enhanced carbon–heteroatom cross-coupling chemistry as it permits the replacement of the aryl halide partner with boronic acids. Nowadays, it is recognized as a powerful synthetic tool whose attractiveness is increasing due to the mild reaction conditions required (e.g., room temperature, weak base, and ambient atmosphere), the ready availability of boronic acids and their derivatives, and its high functional group tolerance.[‌53‌,‌54‌] Chan, Lam, and co-workers also demonstrated that arylboronic esters and triphenylboroxin can be used in place of arylboronic acids in the N-arylation reaction.[‌54‌]

Me 8888, Meeee eeeeeeee e eeeeeeeeee eee eeee-eeee eeeeee-eeeeeeeee eeeeeeee eee eee eeeee eeeeeeee ee eeeeeeeeeee eeeee eee eeeeeeeee eeeeeeeeeeeeeeeeeee eeeee eeee eeeeeee eee eeeeeeeee eeeeeeeee eeeeee (‌Meeeee 88‌).[‌88‌] Mee eeeeeee eeeeeeee eeeeeeeee eeeeee(MM) eeeeeee eeeeeeeeeee eee 8-Å eeeeeeeee eeeeee ee eeeeeeeeeeeeeee ee eeeeeeee eeeeeeee eeeeeeeeeeee eeeee ee eeeeeeeeee ee eeeeee. M eeeee eeeee ee eeeeeeeeee eeeeee eee eeeeeeeee eee eeee eeeee-eeeeeeee eeeeeeee.

‌Meeeee 88‌ Meeeee-Meeeeeeee Meeeeeee ee Meeeeeeeeee Meee Meeeeeeeeee eeee Meeeee[‌88‌]

‌Meeeeeeeeee 88‌

M	M8	M8	Meee (°M) (Meee 8)	Meeee (%)	Mee
MM8M	M	Me	ee	88	[‌88‌]
M(MM)8	M	Me	ee	88	[‌88‌]
MM8M	M	Me	ee	88	[‌88‌]
M(MM)8	M	Me	88	88	[‌88‌]
MM8M	M	e-Me	ee	88	[‌88‌]
M(MM)8	M	e-Me	88	88	[‌88‌]
MM8M	M		ee	88	[‌88‌]
MM8M	M		88	88	[‌88‌]
M(MM)8	M		88	88	[‌88‌]
M(MM)8	(MM8)8M(M)(MM8)8		88	88e	[‌88‌]

e Meeeeeee eeeee eeee ee eee eeeeeeeeeeeee eeee.

Meeeeeeeeeee Meeeeeeee

M-Meeeeeeeeeee (‌88‌, M8 = M; M8 = Me); Meeeeee Meeeeeeee Meeee Meeeeeeee Meeeeeeeeeeeeeeeeeeee:[‌88‌]

M eeeeeeeeee ee MeMM8M (8.888 e, 8.88 eeee), Me(MMe)8•M8M (88.8 ee, 8.888 eeee), eee eeeeeeee 8-Å eeeeeeeee eeeeee (8.888 e) ee MM8Me8 (8.88 eM) eee eeeeeee ee ee eee 8 eee. Me eeee eeeeeeee eeeeeeeeee eee eeeee MeMM8 (8.888 e, 88.8 µM, 8.88 eeee). Mee eeeeeeee eeeeee eee eeee eeeeee eeee e eeeeee eeeeee eee eee eeeeeeee eeee eeeeeee ee 88–88 °M eeeee ee eeeeeeeeee ee M8. Meeee 88 e, eee eeeee eeeeeee eee eeeeeeee eeeeeee e eeee ee Meeeee ee eeeeee eee eeeeeeeee eeeeee eee eee eeeeeeeee eeeeeeeeee eee eeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeeeee eee eeeee eeeeeee eeeeeee. Mee eeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeee/MeMMe 8:8 ee 8:8) ee e eeee eeeeee eee; eeeee: 8.888 e (88%).

References