Mild Rhodium(III)-Catalyzed C–H Allylation with 4-Vinyl-1,3-dioxolan-2-ones: Direct and Stereoselective Synthesis of (<i>E</i>)-Allylic Alcohols

Zhang, Shang‐Shi; Wu, Jia‐Qiang; Lao, Ye‐Xing; Liu, Xu‐Ge; Liu, Yao; Lv, Wenxin; Tan, Dong‐Hang; Zeng, Yao‐Fu; Wang, Honggen

doi:10.1021/ol503229c

Cited by 84 publications

(22 citation statements)

References 53 publications

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“…This redox-neutral transformation occurring at room temperature is rather general as both (hetero) aromatics and di-or trisubstituted olefins were well tolerated. A similar reactivity was also observed when 4-vinyl-1,3-dioxolan-2-ones were employed as coupling partners [79].…”

Section: ð6þsupporting

confidence: 68%

Rh(III)- and Ir(III)-Catalyzed C–C Bond Cross Couplings from C–H Bonds

Wencel‐Delord

Patureau

Glorius

2015

C-H Bond Activation and Catalytic Functionalization I

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(M¼Ir, Rh) is formed and undergoes further transformations, according to the nature of the coupling partner, to finally afford a myriad of valuable, often complex, and otherwise difficult to access scaffolds like heterocycles and polyunsaturated skeletons. The major advances achieved in this field clearly showcase the potential of these catalysts to functionalize latent C-H bonds under surprisingly mild reaction conditions. The aim of this chapter is to present the latest and most representative contributions in the field of Rh(III)-and Ir(III)-catalyzed C-H activation by focusing on the reactivity of the corresponding metallacyclic intermediates.

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Section: ð6þsupporting

confidence: 68%

Rh(III)- and Ir(III)-Catalyzed C–C Bond Cross Couplings from C–H Bonds

Wencel‐Delord

Patureau

Glorius

2015

C-H Bond Activation and Catalytic Functionalization I

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“…Apart from aromatic CÀH activation, olefinic C À Hactivation was also feasible with this catalyst system (Scheme 13;product 1). [43] This type of chemistry was further developed by other groups using different types of directing groups (DGs) towards the synthesis of various allylic alcohol scaffolds (Scheme 13;p roducts 2-4). [44] Recent focus has shifted toward the use of more sustainable,e arth-abundant transition-metal catalysts based on cobalt and manganese.Seminal contributions from both Ackermann and Glorius focused on the Mn I -catalyzed C À Ha llylation of indoles using either ap yridyl or N-pyrimidyl as directing group (Scheme 13; product 4).…”

Section: Allylation Through Càhactivation With Vccsmentioning

confidence: 99%

Catalytic Transformations of Functionalized Cyclic Organic Carbonates

et al. 2018

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Functionalized cyclic organic carbonates and related heterocycles have emerged as highly versatile heterocyclic substrates for ring-opening and decarboxylative catalytic transformations allowing for the development of new stereo- and enantioselective C-N, C-O, C-C, C-S and C-B bond formation reactions. Transition-metal-mediated conversions have only recently been rejuvenated as powerful approaches towards the preparation of more complex molecules. This minireview will highlight the potential of cyclic carbonates and structurally related heterocycles with a focus on their synthetic value and the mechanistic manifolds that are involved upon their conversion.

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“…[20] They are increasingly regarded as key chemicali ntermediates for the preparation of acyclic carbonates and polycarbonates [21] and as ar oute towards cis-diols, [22] methanol, [23] allylic alcohols, [24] ionic liquids, [25] and oxygen-containing heterocyclic compounds. [26] The preparation of cyclic carbonates has long been the domain of organometallic complexes of metals such as Cr,C o, Al, and Sn, [27] which are generally used in combination with co-catalytic amounts of organic nucleophiles.…”

Section: Cycloadditions Of Co 2 To Epoxidesmentioning

confidence: 99%

Cycloadditions to Epoxides Catalyzed by Group III–V Transition‐Metal Complexes

2015

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Complexes of group III–V transition metals are gaining increasing importance as Lewis acid catalysts for the cycloaddition of dipolarophiles to epoxides. This review examines the latest reports, including homogeneous and heterogeneous applications. The pivotal step for the cycloaddition reactions is the ring opening of the epoxide following activation by the Lewis acid. Two modes of cleavage (CC versus CO) have been identified depending primarily on the substitution pattern of the epoxide, with lesser influence observed from the Lewis acid employed. The widely studied cycloaddition of CO2 to epoxides to afford cyclic carbonates (CO bond cleavage) has been scrutinized in terms of catalytic efficiency and reaction mechanism, showing that unsophisticated complexes of group III–V transition metals are excellent molecular catalysts. These metals have been incorporated, as well, in highly performing, recyclable heterogeneous catalysts. Cycloadditions to epoxides with other dipolarophiles (alkynes, imines, indoles) have been conducted with scandium triflate with remarkable performances (CC bond cleavage).

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Mild Rhodium(III)-Catalyzed C–H Allylation with 4-Vinyl-1,3-dioxolan-2-ones: Direct and Stereoselective Synthesis of (E)-Allylic Alcohols

Cited by 84 publications

References 53 publications

Rh(III)- and Ir(III)-Catalyzed C–C Bond Cross Couplings from C–H Bonds

Rh(III)- and Ir(III)-Catalyzed C–C Bond Cross Couplings from C–H Bonds

Catalytic Transformations of Functionalized Cyclic Organic Carbonates

Cycloadditions to Epoxides Catalyzed by Group III–V Transition‐Metal Complexes

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