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. Author manuscript; available in PMC: 2019 Jun 28.
Published in final edited form as: J Am Chem Soc. 2017 Nov 20;139(48):17293–17296. doi: 10.1021/jacs.7b10519

Table 1.

Ni-Catalyzed Conjunctive Cross-Coupling with C(sp3) Electrophiles

graphic file with name nihms-1026333-t0003.jpg
entry E-X ligand Ni salt % yielda er
1 2 none Ni(acac)2 <10% nd
2 2 L1 Ni(acac)2 <10% nd
3 2 L2 Ni(acac)2 <10% nd
4 2 L3 Ni(acac)2 <10 nd
5 2 L4 Ni(acac)2 <5% nd
6b 2 L5 Ni(acac)2 17 89:11
7b 2 L6 Ni(acac)2 36 99:1
8b,c 2 L6 Ni(acac)2 49 98:2
9b,c 2 L6 [(methallyl)NiCI]2 51 98:2
10b,c 2 L7 [(methallyl)NiCI]2 70 98:2
11b,c 3 L7 Ni(acac)2 34 50:50
12d 3 Ni(acac)2 92 nd
(a)

Determined by NMR versus an internal standard.

(b)

Determined by chiral SFC analysis.

(c)

Catalyst solution pre-complexed for 1.5 h.

(d)

Reaction conducted at 22 °C without ligand and with one equivalent NaI added.