Nature Communications

Table 4 Scope of the 3-catalyzed asymmetric A³-coupling reactions^a

From: Photothermal conversion triggered thermal asymmetric catalysis within metal nanoparticles loaded homochiral covalent organic framework


Entry	R₁	R₂	R₃ R₄	Yield (%)^b	ee (%)^b	TON
1	Ph−	Ph−	−(CH₂)₄−	98	96 (S)	46.7
2	Ph−	4-Me−Ph−	−(CH₂)₄−	92	96 (S)	43.8
3	Ph−	4-MeO−Ph−	−(CH₂)₄−	90	94 (S)	42.9
4	Ph−	4-NO₂−Ph−	−(CH₂)₄−	96	98 (S)	45.7
5	Ph−	4-F−Ph−	−(CH₂)₄−	97	98 (S)	46.2
6	4-Me−Ph−	Ph−	−(CH₂)₄−	94	95 (S)	44.8
7	4-MeO−Ph−	Ph−	−(CH₂)₄−	95	98 (S)	45.2
8	4-NO₂−Ph−	Ph−	−(CH₂)₄−	86	92 (S)	41.0
9	4-F−Ph−	Ph−	−(CH₂)₄−	88	95 (S)	41.9
10	4-Me−Ph−	4-NO₂−Ph−	−(CH₂)₄−	95	98 (S)	45.2
11	4-MeO−Ph−	4-NO₂−Ph−	−(CH₂)₄−	95	98 (S)	45.2
12	4-NO₂−Ph−	4-NO₂−Ph−	−(CH₂)₄−	83	95 (S)	39.5
13	4-F−Ph−	4-NO₂−Ph−	−(CH₂)₄−	84	95 (S)	40.0
14	4-Me−Ph−	4−Me−Ph−	−(CH₂)₄−	86	93 (S)	41.0
15	4-MeO−Ph−	4-Me−Ph−	−(CH₂)₄−	84	91 (S)	40.0
16	4-NO₂−Ph−	4-Me−Ph−	−(CH₂)₄−	91	94 (S)	43.3
17	4-F−Ph−	4-Me−Ph−	−(CH₂)₄−	92	95 (S)	43.8
18	Ph−	Ph−	−(CH₂)₂O(CH₂)₂−	68	90 (S)	32.4
19	Ph−	Ph−	−(CH₂)₅−	95	95 (S)	45.2
20	3-Me−Ph−	Ph−	−(CH₂)₄−	98	96 (R)	46.7
21	3-MeO−Ph−	Ph−	−(CH₂)₄−	98	94 (R)	46.7
22	3-NO₂−Ph−	Ph−	−(CH₂)₄−	86	95 (R)	41.0
23	3-Me−Ph−	4-Me−Ph−	−(CH₂)₄−	87	91 (R)	41.4
24	3-Me−Ph−	4-NO₂−Ph−	−(CH₂)₄−	95	95 (R)	45.2
25	3-NO₂−Ph−	4-Me−Ph−	−(CH₂)₄−	94	93 (R)	44.8
26	3-NO₂−Ph−	4-NO₂−Ph−	−(CH₂)₄−	86	94 (R)	41.0
27	9-anthral	Ph−	−(CH₂)₄−	37	87 (S)	17.6
28	Fluorene-2-carboxal	Ph−	−(CH₂)₄−	38	89 (S)	18.1

^aReaction conditions: N₂, 3 (4.5 mg, 2.1 mol% Pd), aromatic aldehyde (0.5 mmol), aromatic alkyne (0.5 mmol) and secondary amine (0.75 mmol), p-dioxane (2 mL), r.t., 300 W xenon with a power density of 2.5 W cm⁻² (λ > 400 nm)
^bYield and ee are determined by GC and chiral HPLC, respectively (Supplementary Figs. 30 and 31)

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