Organic Letters
Letter
(2) (a) Yamamura, M.; Moritani, I.; Murahashi, S.-I. J. Organomet.
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MS. However, these results did not necessarily indicate that
this reaction went through a radical pathway, in comparison to
control experiments (Scheme 5b). It is clear that substrate 2a
cannot react with TEMPO, but the other reagent, n-
butyllithium could be coupled with TEMPO directly even
without any iron catalysts. Combined with our previous
experiments (Schemes 5a,b), there is therefore no clear
evidence to support the notion that the decreasing yield is
caused by the trapped radical or the insufficient lithium
reagents. Furthermore, the reaction of 10 was carried out and
monitored very carefully (Scheme 5c), but only trace
isomerization product 1c was observed (Z/E > 15:1). On
the other hand, radical clock experiments of 19 and 20 were
also performed. The results indicated that no ring-closing
product 19a or ring-opening product 20a was observed,
therefore hinting at the absence of transient radical
intermediates (Scheme 5d). These studies suggested that
radical pathways were not likely to be involved in this reaction.
In conclusion, an effective stereospecific Fe(II)-catalyzed
alkenylalkyl cross-coupling reaction was developed. More than
30 examples were obtained with moderate to good yields. The
reaction can be scaled up to gram scale, and further
transformations of the iron-catalyzed cross-coupling reaction
products were explored. The plausible reaction mechanism was
proposed on the basis of our controlled experiments and
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ASSOCIATED CONTENT
* Supporting Information
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1489. (b) Tamura, M.; Kochi, J. K. Synthesis 1971, 1971, 303−305.
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The Supporting Information is available free of charge on the
55, 11188−11192. (b) Tindall, D. J.; Krause, H.; Fu
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Experimental procedures, product characterization data
(8) (a) Agata, R.; Iwamoto, T.; Nakagawa, N.; Isozaki, K.;
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AUTHOR INFORMATION
Corresponding Authors
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ORCID
(10) (a) Benischke, A. D.; Breuillac, A. J. A.; Moyeux, A.; Cahiez, G.;
Knochel, P. Synlett 2016, 27, 471−476. (b) Cahiez, G.; Gager, O.;
Buendia, J.; Patinote, C. Chem. - Eur. J. 2012, 18, 5860−5863.
(c) Cahiez, G.; Foulgoc, L.; Moyeux, A. Angew. Chem., Int. Ed. 2009,
48, 2969−2972.
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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(11) Jia, Z.; Liu, Q.; Peng, X.-S.; Wong, H. N. C. Nat. Commun.
2016, 7, 10614.
This work was supported by NSFC (21672181/21272199),
GRF/RGC (CUHK14309216/CUHK14303815/403012),
NSFC/RGC Joint Research Scheme (N_CUHK451/13),
Shenzhen Science and Technology Innovation Committee
(JCYJ20160608151520697), a grant to the State Key
Laboratory of Synthetic Chemistry and Guangdong-HK
Technology Cooperation Funding Scheme (GHP/004/
16GD) from the Innovation and Technology Commission,
The Chinese Academy of Sciences-Croucher Foundation
Funding Scheme for Joint Laboratories, and Direct Grants
(4053325) from The Chinese University of Hong Kong.
(12) Liu, Q.; Wang, Z.-Y.; Peng, X.-S.; Wong, N. H. C. J. Org. Chem.
2018, 83, 6325−6333.
(13) Toummini, D.; Ouazzani, F.; Taillefer, M. Org. Lett. 2013, 15,
4690−4693.
(14) Li, Y.; Zhang, L.; Zhang, Z.; Xu, J.; Pan, Y.; Xu, C.; Liu, L.; Li,
Z.; Yu, Z.; Li, H.; Xu, L. Adv. Synth. Catal. 2016, 358, 2148−2155.
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