Synergistic Ni/Cu catalyzed migratory arylsilylation of terminal olefins

Zhao, Binzhi; Li, Yuqiang; Li, Haoyang; Belal, Md.; Zhu, Lei; Yin, Guoyin

doi:10.1016/j.scib.2020.10.001

Cited by 28 publications

(7 citation statements)

References 63 publications

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“…However, the silylative difunctionalization of alkenes using Si−M reagents is rare. Sporadic examples of direct arylsilylation of unactived alkenes by palladium‐ [9] and nickel/copper catalysis [10] were only recently reported, which largely relied on the use of difficultly accessible Si−B as the pronucleophiles (Scheme 1a; top right) [11] . The type of R 3 Si−ZnCl reagent, which was prepared by a facile transmetalation from Si−Li with ZnCl 2 , has also proven to be an alternative choice in the nickel‐catalyzed silylacylation of vinylarenes, as reported by Brown and co‐workers (Scheme 1a; bottom right) [12] .…”

Section: Methodsmentioning

confidence: 99%

Salt‐Stabilized Silylzinc Pivalates for Nickel‐Catalyzed Carbosilylation of Alkenes

et al. 2022

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We herein report the preparation of solid and salt-stabilized silylzinc pivalates from the corresponding silyllithium reagents via transmetalation with Zn(OPiv) 2 . These resulting organosilylzinc pivalates show enhanced air and moisture stability and unique reactivity in the silylative difunctionalization of alkenes. Thus, a practical chelation-assisted nickel-catalyzed regioselective alkyl and benzylsilylation of alkenes has been developed, which provides an easy method to access alkyl silanes with broad substrate scope and wide functional group compatibility. Kinetic experiments highlight that the OPiv-coordination is crucial to improve the reactivity of silylzinc pivalates. Furthermore, late-stage functionalizations of druglike molecules and versatile modifications of the products illustrate the synthetical utility of this protocol.

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Section: Methodsmentioning

confidence: 99%

Salt‐Stabilized Silylzinc Pivalates for Nickel‐Catalyzed Carbosilylation of Alkenes

et al. 2022

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“…Finally, the [Ni]-alkyl complexes couple with various electrophiles to produce the functionalized products (Scheme 1b). The coupling mechanisms mainly involve various nickel intermediates such as [Ni]-H, 14,15 [Ni]-CR n , 16 [Ni]-SiR 3 17 and [Ni]-Bpin complexes. Moreover, [Ni]-Bpin complexes have been widely used in reductive cross-coupling reactions 18 and twocomponent functionalization reactions such as the boration of electrophiles.…”

Section: Yang Yementioning

confidence: 99%

Recent progress in nickel-catalyzed carboboration of alkenes

Lin

Mao

et al. 2022

Org. Biomol. Chem.

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“…However, the reactive intermediate restricted the functional group compatibility. Until recently, arylsilylation, alkenylsilylation and silylacylation of C-C double bonds using Si-M (M = B, Zn) reagents were reported by Eagle 61 , Yin 60 , and Brown 59 groups, respectively (Fig. 1a ).…”

Section: Introductionmentioning

confidence: 99%

Regioselective Ni-Catalyzed reductive alkylsilylation of acrylonitrile with unactivated alkyl bromides and chlorosilanes

Sun

Zhou

et al. 2022

Nat Commun

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Transition-metal catalyzed carbosilylation of alkenes using carbon electrophiles and silylmetal (-B, -Zn) reagents as the nucleophiles offers a powerful strategy for synthesizing organosilicones, by incorporating carbon and silyl groups across on C-C double bonds in one step. However, to the best of our knowledge, the study of silylative alkenes difunctionalization based on carbon and silyl electrophiles remains underdeveloped. Herein, we present an example of silylative alkylation of activated olefins with unactivated alkyl bromides and chlorosilanes as electrophiles under nickel catalysis. The main feature of this protocol is employing more easily accessible substrates including primary, secondary and tertiary alkyl bromides, as well as various chlorosilanes without using pre-generated organometallics. A wide range of alkylsilanes with diverse structures can be efficiently assembled in a single step, highlighting the good functionality tolerance of this approach. Furthermore, successful functionalization of bioactive molecules and synthetic applications using this method demonstrate its practicability.

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Synergistic Ni/Cu catalyzed migratory arylsilylation of terminal olefins

Cited by 28 publications

References 63 publications

Salt‐Stabilized Silylzinc Pivalates for Nickel‐Catalyzed Carbosilylation of Alkenes

Salt‐Stabilized Silylzinc Pivalates for Nickel‐Catalyzed Carbosilylation of Alkenes

Recent progress in nickel-catalyzed carboboration of alkenes

Regioselective Ni-Catalyzed reductive alkylsilylation of acrylonitrile with unactivated alkyl bromides and chlorosilanes

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