Table 4.

Carboamination of N-Protected Hex-4-enylamines^a

Entry	Amine	Aryl bromide	Product	Rxn. Time (h)	Yield (%) b
1				23	59
2	25			36	50
3	25			44	44 e
4				42	43 e,f
5	27			30	43 e,f, g
6				27	55 e
7	28			21	55 e
8	28			31	60 e,h
9	28			53	62 e
10				53	49 e
11	29			53	44 e,g

^aConditions: 1.0 equiv amine, 1.2 equiv ArBr, 2.3 equiv Cs₂CO₃, 5 mol % Pd(OAc)₂, 7.5 mol % Nixantphos, dioxane (0.25 M), 100 °C.

^bYield refers to average isolated yield obtained in two or more experiments. All reactions proceeded with >20:1 diastereoselectivity.

^cAr = 3-nitrophenyl.

^dAr = 4-carbomethoxyphenyl.

^e(±)-BINAP used in place of Nixantphos.

^fA trace amount (ca. 1–5%) of a regioisomer analogous to 31 and 33 was also obtained.

^gThis reaction was conducted with 2.0 equiv ArBr, 10 mol % Pd(OAc)₂ and 15 mol % (±)-BINAP.

^hThis reaction proceeded to 94% conversion.