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. Author manuscript; available in PMC: 2018 Aug 23.
Published in final edited form as: J Am Chem Soc. 2017 Aug 14;139(33):11595–11600. doi: 10.1021/jacs.7b06794

Table 1.

Identification of a catalytic system for the carbocyclization of unactivated alkyl bromides.

graphic file with name nihms907202u2.jpg
entry catalyst ligand base solvent yield (%)a
1 [Pd(allyl)Cl]2 IMes iPr2NEt PhMe <2
2b Pd(PPh3)4 – PMP PhtBu <2
3 Pd(OAc)2 dtbdppf iPr2NEt PhMe 5
4 Pd(OAc)2 dcypf iPr2NEt PhMe <2
5 Pd(OAc)2 dippf iPr2NEt PhMe <2
6 Pd(OAc)2 dtbpf iPr2NEt PhMe 30(3)
7 [Pd(allyl)Cl]2 dtbpf iPr2NEt PhMe 65(12)
8 [Pd(allyl)Cl]2 dtbpf Et3N PhMe 73(5)
9 [Pd(allyl)Cl]2 dtbpf Et3N PhCF3 85(5)
10 Pd(dtbpf)Cl2 – Et3N PhCF3 14(2)
a

Yield determined by 1H NMR spectroscopy using 1,3,5-trimethoxybenzene as internal standard. Yield in parenthesis is that of a minor regioisomer, see Supporting Information for details.

b

Reaction temperature 130 °C.