Advanced Synthesis & Catalysis
10.1002/adsc.201801586
1
by H NMR (CDCl
3
, 400 MHz) and/or GC-MS to obtain
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conversion, yield and selectivity using internal standard
and comparison with authentic samples. Purification by
chromatography on silica gel (EtOAc/hexanes) afforded
the title product.
[
[
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Representative Procedure for Nickel-Catalyzed C(sp )–
3
C(sp ) Cross-Coupling. 1.0 g Scale. An oven-dried, two-
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necked flask (100 mL) equipped with a stir bar was
charged with naphthalen-1-yl 4-methylbenzenesulfonate
(
0
3
1.00 g, 3.35 mmol, 1.0 equiv) and Ni(dppe)Cl
2
(1.77 mg,
4 9
.10 mol%). A solution of n-C H MgCl (2.0 M in THF,
.35 mL, 2.0 equiv) was added dropwise with vigorous
stirring at room temperature and the reaction mixture was
stirred for 24 h at 23 °C. After the indicated time, the
reaction mixture was diluted with HCl (1.0 N, 10 mL) and
Et
2
O (1 x 100 mL), the organic layer was extracted with
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HCl (1.0 N, 2 x 15 mL) and NaOH (1.0 N, 2 x 15 mL), the
organic layers were combined, dried and concentrated. A
1
sample was analyzed by H NMR (CDCl
3
, 400 MHz) and
GC-MS to obtain conversion, yield and selectivity using
internal standard and comparison with authentic samples.
Purification by chromatography on silica gel
(
EtOAc/hexanes) afforded the title product; 98% (0.603 g).
2
353; e) H. Zeng, Z. Qiu, A. Dominguez-Huerta, Z.
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Acknowledgements
5
We gratefully acknowledge Narodowe Centrum Nauki (grant no.
2018, 54, 12286-12301; g) E. Bisz, M. Szostak,
ChemSusChem 2017, 10, 3964-3981.
2
014/15/D/ST5/02731, A.P., M.S.), Rutgers University (M.S.) and
the NSF (CAREER CHE-1650766) for generous financial support.
[
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