Science of Synthesis

Zhang, H.; Liu, C.; Lei, A., Science of Synthesis: Catalytic Transformations via C—H Activation, (2015) 2, 167.

Various hetarenes ‌51‌ are converted into the corresponding heterocyclic carboxylic esters ‌52‌ in moderate to good yields through palladium-catalyzed aerobic oxidative C—H carbonylation (‌Scheme 27‌).[‌38‌] Substituted N-alkylindoles, thiophenes, and benzothiophenes ‌51‌ are suitable substrates under the standard reaction conditions. This transformation shows remarkably high regioselectivity.

‌Meeeee 88‌ Meeeeeeee-Meeeeeeee M—M Meeeeeeeeeeee ee Meeeeeeee[‌88‌]

‌Meeeeeeeeee 88‌

Me8	M8	Meeeee (%)	Mee
	Me	88	[‌88‌]
	Me	88	[‌88‌]
	Me	88	[‌88‌]
	Me	88	[‌88‌]
	Me	88	[‌88‌]
	Me	88	[‌88‌]
	Me	88	[‌88‌]
	Me	88	[‌88‌]
	Me	88	[‌88‌]
	Me	88e	[‌88‌]
	(MM8)8Me	88	[‌88‌]
	(MM8)88Me	88	[‌88‌]
	(MM8)8eMe	88	[‌88‌]
	MM(Me)(MM8)8Me	88	[‌88‌]
	MM(Me)(MM8)8Me	88	[‌88‌]
	MM(Me)(MM8)8Me	88	[‌88‌]
	Me	88	[‌88‌]
	Me	88	[‌88‌]
	Me	88	[‌88‌]
	Me	88	[‌88‌]
	Me	88e	[‌88‌]
	Me	88 (88)e,e	[‌88‌]
	Me	88e	[‌88‌]
	MM(Me)(MM8)8Me	88e	[‌88‌]

e Meeeeeee eeeeee.

e 88 e.

e 88 °M.

e Mee eeeeeee eeee eeeeee; eeeeeeee eeeee ee M8 eeeeeeeeeeee eeeeeee ee eeeeeeeeeee.

e Meeeeeeeee: MeMe8(MMe8)8 (8 eee%), Me8M (88 eee%), Me(MMe)8 (8 eeeee), 888 °M, 88 e.

Meeeeee eeeeeeeeeee eeeeeee ‌88‌ (M8 ≠ M) ee eeee ee eeeeeee ‌88‌ (M8 = M) eeee eeee MM eee eeeeeeeeeeee eeee eeeeee eee eeeeee eeeeeeee ee eeee eee eeeeeee eeeeee-8-eeeeeeeeeeee ‌88‌ ee eee eeeeeeee ee e eeeeeee eeeeeeee (‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ Meeeeee-Meeeeeeee M—M Meeeeeeeeeeee ee Meeeeeeee[‌88‌]

‌Meeeeeeeeee 88‌

e Meeeeeee eeeeee.

e 88 °M, 88 e.

Meeeeeeeeeee Meeeeeeee

Meeee Meeeeeeeeeeeeeeeeeee ‌88‌; Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeeee eeeeeeee ee eeeeeeeee eeeeeeeee eee eeeee, eee eeeeeeee ee eeeeee eeeeeeeeeeeeee eee eeeeeee eeee ee e eeee.

MeMe8(MMe8)8 (8.8 ee, 8.8 eee%), Me8M (8.8 ee, 8 eee%), eee e eeeeeeee ‌88‌ (8.8 eeee) eeee eeeeeeee ee ee eeee-eeeee Meeeeee eeee eeeeeeee eeee e eeeeeee eee. Me(MMe)8 (8.8 ee, 88 eee%) eee eeeee ee eee eeee ee e eeeeeeee. M eeeeeee eeeeee eeee MM eee eee (8:8) eee eeeeeeeee ee eee Meeeeee eeee eee eee eeee eeee eee eee eeee eee eeeeee eeeee eeeee. Me eeeeeee (M8MM; 8.8 eM), MMMM (8.8 eM), eee eeeeeee (8.8 eM) eeee eeeee ee eee eeee eee eeeeeee. Mee Meeeeee eeee eee eeeeee ee 888 °M eee 88 e eee eeee eeeeee ee ee. Mee eee eeeeeee eee eeeeeeeee eeeeeeee, eee eeeeeeee eee eeeeeeee eeee M8M, eee eee eeeeeee eee eeeeeeeee eeee MM8Me8 (8 ×). Mee eeeeeeee eeeeeee eeeeee eeee eeeee (Me8MM8) eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe/Me8M).

Meeee Meeeee-8-eeeeeeeeeeee ‌88‌; Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeeee eeeeeeee ee eeeeeeeee eeeeeeeee eee eeeee, eee eeeeeeee ee eeeeee eeeeeeeeeeeeee eee eeeeeee eeee ee e eeee.

Me eeeeee ‌88‌ (8.8 eeee), {MeMe(eee)}8 (8.88 eeee), M8M8M8 (8.8 eeee), ee eeeeeee (M8MM; 8.8 eeee), eee eeeeeee (8.8 eM) eeee eeeee ee e 88-eM Meeeeee eeee. Mee eeeee eeee eee eeeeeeeee eee eeeeee eeee MM (88.88% eeeeee) eeeee eeeee eeeeee ee eee eeeeeee eeeeeeeeeee eeee MM eee (8.8 eee). Mee eeee eee eeeeeee eeeee-eeeeee eee eeeeeeee ee ee eee eeee eeeeeeeee ee 888 °M. Mee eeeeeee eee eeeeeee eee 88 e eee eeee eeeeee ee ee. Meeeee MM eee eeeeeeeeee eee eee eeeeeeeee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee 888–888 eeee, eeeeeeeee eeeee/MeMMe 88:8 ee 8:8).

References