. Author manuscript; available in PMC: 2025 Aug 25.

Published in final edited form as: Adv Synth Catal. 2024 Jan 9;366(4):1013–1018. doi: 10.1002/adsc.202301222

Table 3.

Substrate scope, stereo- and regioselectivities of Ru-catalyzed hydroacyloxylations.


entry	alkyne	carboxylic acid	catalyst	combined yield^[a]	isomer ratio^[b] (E) : (Z) : Markovnikov	vinylic ester products
1			9	79%	68 : 27 : 5	(E)-33 : (Z)-33 : 34
2			19+11	65%	19:81 :0	(E)-33 : (Z)-33 : 34
3			9	63%	81 : 13 : 6	(E)-35 : (Z)-35 : 36
4			19+11	41%	22:77 :1	(E)-35 : (Z)-35 : 36
5			9	53%	57 : 23 : 20	(E)-37 : (Z)-37 : 38
6			19+11	41%	15 : 83 : 2	(E)-37 : (Z)-37 : 38
7			9	83%	55 : 39 : 6	(E)-39 : (Z)-39 : 40
8			19+11	73%	15 : 85 : 0	(E)-39 : (Z)-39 : 40
9			9	73%	71 : 25 : 4	(E)-41 : (Z)-41 : 42
10			19+11	70%	20:79 :1	(E)-41 : (Z)-41 : 42
11			9	81%	33 : 13 : 54	(E)-43 : (Z)-43 : 44
12			19+11	82%	17:68 :15	(E)-43 : (Z)-43 : 44
13			9	69%	50 : 35 : 15	(E)-45 : (Z)-45 : 46
14			19+11	35%	37:50 :13	(E)-45 : (Z)-45 : 46
15			9	41%	33 : 29 : 38	(E)-47 : (Z)-47 : 48
16			19+11	73%	31:48 :21	(E)-47 : (Z)-47 : 48

^[a]

Combined yield of (E), (Z), and Markovnikov isomers, after chromatographic separation from other materials.

^[b]

Vinylic ester isomers were chromatographically inseparable. Isomer ratios were determined by ¹H NMR integration of diagnostic alkene resonances in the product mixture, prior to chromatographic purification.