Visible Light‐Initiated C(sp3)Br/C(sp3)H Functionalization of α‐Carbonyl Alkyl Bromides through Hydride Radical Shift

Li, Yang; Liu, Bang; Song, Ren‐Jie; Wang, Qiuan; Li, Jin‐Heng

doi:10.1002/adsc.201501134

Cited by 70 publications

(20 citation statements)

References 120 publications

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“…In 2016, Xia and co-workers reported a visible light induced 1,7-enyne cascade bicyclization reaction [113] (Scheme 17). Similarly, visible light induced cascade cyclization reactions were reported by Li and Wang [114], Kumar [115], and Li [116]. Other radical precursors such as the thiyl radical could also be used in similar tandem cyclization reactions [117,118].…”

Section: Other Csp 3 Radical Reagentsmentioning

confidence: 59%

Visible light promoted difunctionalization reactions of alkynes

Ren

2019

Chinese Journal of Catalysis

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Visible light promoted difunctionalization of alkynes is reviewed. The difunctionalization reaction is achieved by different reagents. Radicals such as carbon (sp 3), carbon (sp 2), and other heteroatom (P, S, N, Se, O, and halide) radicals initiated by visible light can undergo radical addition to a carbon-carbon triple bond. Upon further transformation, the desired difunctionalized products are obtained. Some organometallic complexes can be activated by visible light; the difunctionalization of alkynes is catalyzed by these species. Other reagents like 1,3-dipole precursors could also react with alkynes to give difunctionalization products; here, the 1,3-dipole derivatives are obtained by visible light photocatalysis. So far, the strategy has been succeeded in the formation of CC bonds and C-X bonds. Several valuable chemical skeletons have been constructed under mild conditions. However, high regio-and stereoselectivities in some direct difunctionalization methodologies are yet to be achieved.

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Section: Other Csp 3 Radical Reagentsmentioning

confidence: 59%

Visible light promoted difunctionalization reactions of alkynes

Ren

2019

Chinese Journal of Catalysis

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“…2016 年, 李金恒课题组 [96] 巧妙地设计了 α-溴代羰 [102] 利用 N-甲基-N-烯丙基苯甲酰胺为底物, 异丙醇为溶剂及自由基源, 在氧化剂叔丁基过氧化物(DTBP)引发下, 通过自由基加成环化合成了一系列羟烷基化的异喹啉酮衍生物. 该课题组 [103] 在后续研究中, 用烷烃类溶剂代替异丙醇参与反应, 在相同条件下, 也能顺利得到烷基化的异喹啉酮衍生物(图 52).…”

Section: 自由基加成环化合成喹啉衍生物unclassified

Synthesis of Oxygen- or Nitrogen-Containing Heterocyclic Compounds via Radical Addition Cascade Cyclization

Zhang¹,

Liu²,

Sun³

2021

Chinese Journal of Organic Chemistry

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Oxygen-or nitrogen-containing heterocyclic compounds have been widely applied in pharmaceuticals, chemical products and materials, and the synthesis of these compounds has drawn much attention. One of the convenient and efficient strategies for the construction of various oxygen-or nitrogen-containing heterocycles is radical addition cascade cyclization in recent years. This article offers an overview on the radical addition cascade cyclization strategies based on the types of oxygenor nitrogen-containing heterocyclic compounds.

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“…Our group also reported a new visible‐light‐initiated C−Br/C−H functionalization of 1, n ‐enynes ( n= 6, 7) with α‐carbonyl alkyl bromides through a 1,5‐hydride radical shift strategy for the synthesis of five‐membered carbocyclic ring‐fused polycyclic hydrocarbons (Scheme ) . It was noted that the value of the turnover number (TON) was up to 4.93×10 3 .…”

Section: Annulation Of 1n‐enynesmentioning

confidence: 99%

Developments in the Chemistry of α‐Carbonyl Alkyl Bromides

Ouyang

Song

2018

Chemistry An Asian Journal

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α-Carbonyl alkyl bromides are powerful reactive species for the formation of carbon-carbon bonds. Strategies relying on intermolecular C-H functionalization and cross-coupling reactions, also referred to as intramolecular cyclization, have been employed for the construction of alkenes, alkanes, ketones, and other natural-product-like ring compounds from simple alkynes, alkenes, and 1,n-enynes. In view of the importance of these α-carbonyl alkyl bromides, especially the difluoro carbonyl alkyl bromides, many researchers have focused their efforts to develop facile and mild synthetic methods for compounds with important biological activities. This review aims to briefly discuss the latest developments in the transformation of α-carbonyl alkyl bromides with emphasis on the related reaction mechanisms.

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Visible Light‐Initiated C(sp³)Br/C(sp³)H Functionalization of α‐Carbonyl Alkyl Bromides through Hydride Radical Shift

Abstract: An ew visible light-initiated 1,5-hydride radical shift strategy has been developed to enable the one-stepf unctionalization of bothaC(sp

Cited by 70 publications

References 120 publications

Visible light promoted difunctionalization reactions of alkynes

Visible light promoted difunctionalization reactions of alkynes

Synthesis of Oxygen- or Nitrogen-Containing Heterocyclic Compounds via Radical Addition Cascade Cyclization

Developments in the Chemistry of α‐Carbonyl Alkyl Bromides

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