Table 3.

Synthesis of Isoindole-1,3-diones by the Aminocarbonylative Cyclization of o-Halobenzoate Esters^a

entry	o-halo easter	amine	product	% isolated yield
1				89
2	1a	2a	3a	85b
3		2a	3a	55
4		2a		46
5		2a		51
6		2a		71
7	1a			81
8	1a			92
9	1a			25
10	1a	2d	3g	41c
11	1a			68
12	1a			61
13	1a			77
14	1a			71
15	1a			79
16	1a			77
17	1a			71
18	1a			68
19	1a			57
20	1a			25
21	1a			62
22	1a			61
23	1a			57
24	1a			55
25	1a			61
26	1a			62
27	1a			55

^aRepresentative procedure: o-halobenzoate ester 1 (0.5 mmol), amine 2 (1.2 equiv), Pd(OAc)₂ (5 mol %), dppp (10 mol %), Cs₂CO₃ (2 equiv), and toluene (6 mL) were placed in a round-bottomed flask. The flask was sealed and flushed with CO. The reaction was stirred at 95 °C for 24 h with a CO balloon on top of the flask.

^bThe reaction was scaled up to 2 mmol of halo ester.

^cThe reaction was carried out with 10 equiv of amine.