10.1002/adsc.201900327
Advanced Synthesis & Catalysis
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Scheme 5. Gram-scale synthesis and further transformation of 3a.
Compared with our previous report,[18] an additional
migratory insertion of alkyne was presented in this reaction.
Following by an intramolecular Heck-type reaction, β-H
elimination, cyclopropane ring-opening, and final cyclization
provided a series of spirocyclic compounds containing indene
and 1,2-dihydronaphthalene moieties (see Scheme S6 in SI).
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summary,
a
facile
palladium(II)-catalyzed
2
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General Procedure for Synthesis of 3
To
a
flame-dried sealing tubes were added the
methylenecyclopropanes 1 (0.20 mmol, 1.0 equiv), alkynes 2
(0.40 mmol, 2.0 equiv), Pd(MeCN)2Cl2 (0.02 mmol, 0.1 equiv), t-
BuXphos (0.02 mmol, 0.1 equiv) and cesium carbonate (0.40
mmol, 2.0 equiv), and the flask was evacuated and backfilled with
Ar for 3 times. Toluene (2.0 mL) was added to this flask via a
syringe under Ar. The reaction mixture was stirred for 9 hours at
130 oC. Appropriate amount of silica gel was added to the
reaction mixture and the solvent was removed under vacuum
pump at low temperature. Then, the crude product was purified by
a silica gel chromatography (PE) to get the desired products 3 in
44-93% yields.
Acknowledgements
We are grateful for financial support from the National Basic
Research Program of China [(973)-2015CB856603], the
Strategic Priority Research Program of the Chinese Academy of
Sciences (Grant No. XDB20000000) and sioczz201808, and the
National Natural Science Foundation of China (Nos. 20472096,
21372241, 21572052, 20672127, 21421091, 21372250, 21121062,
21302203, 20732008, 21772037, 21772226, and 21861132014).
[18] W. Fang, Y. Wei, M. Shi, Org. Lett. 2018, 20, 7141.
[19] CCDC-1885428 contains the supplementary crystallographic data for
this paper. These data can be obtained free of charge from The
Cambridge
Crystallographic
Data
Centre
4
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