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

ABSTRACT: 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.

SUBMITTER: Chen Y

PROVIDER: S-EPMC8115222 | biostudies-literature | 2021 Jan

REPOSITORIES: biostudies-literature

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

Chen Yu Y Zhang Xiao X Liu Fang F He Gucheng G Zhang Ju J Houk K N KN Smith Amos B AB Liang Yong Y

Chinese chemical letters = Zhongguo hua xue kuai bao 20210101 1

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 - wo ...[more]

PMID: 33994753

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