Citation: Yu Chen, Xiao Zhang, Fang Liu, Gucheng He, Ju Zhang, K.N. Houk, Amos B. Smith Ⅲ, Yong Liang. The role of CuI in the siloxane-mediated Pd-catalyzed cross-coupling reactions of aryl iodides with aryl lithium reagents[J]. Chinese Chemical Letters, ;2021, 32(1): 441-444. doi: 10.1016/j.cclet.2020.05.009 shu

The role of CuI in the siloxane-mediated Pd-catalyzed cross-coupling reactions of aryl iodides with aryl lithium reagents

Yu Chen ^{a, 1} ,
Xiao Zhang ^{a, 1} ,
Fang Liu ^a ,
Gucheng He ^a ,
Ju Zhang ^a ,
K.N. Houk ^{c, *} ,
Amos B. Smith Ⅲ ^{b, *} ,
Yong Liang ^{a, *}

a.
State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China
b.
Department of Chemistry, University of Pennsylvania, PA 19104, United States
c.
Department of Chemistry and Biochemistry, University of California, CA 90095, United States

houk@chem.ucla.edu

smithab@sas.upenn.edu

yongliang@nju.edu.cn

Received Date: 12 March 2020
Revised Date: 30 April 2020
Accepted Date: 9 May 2020
Available Online: 14 May 2020

Figures(3)

Experiments indicate that a catalytic amount of CuI plays an important role in the siloxane-mediated Pd-catalyzed cross-coupling reactions with the direct use of organolithium reagents. Addition of organolithium to the siloxane transfer agent generates an organosilicon intermediate. DFT calculations indicate that CuI initially accelerates the Si-Pd(Ⅱ) transmetalation of the organosilicon intermediate by the formation of CuI₂^-. Subsequently, CuI₂^- works as a shuttle between the Si-Cu(I) and Cu(I)-Pd(Ⅱ) transmetalation processes.
- Cross-coupling,
- CuI,
- DFT calculation,
- Reaction mechanism,
- Transmetalation
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