Direct deoxygenative borylation DOI Creative Commons
Jianbin Li

Pure and Applied Chemistry, Год журнала: 2022, Номер 94(11-12), С. 1209 - 1224

Опубликована: Дек. 1, 2022

Abstract Direct deoxygenative borylation is a highly enabling chemical transformation considering the attractive synthetic features of oxygenous feedstocks and organoboron compounds. Despite ranking among ideality in different settings, such space remained largely uncharted underutilized until recent decades. This short review will summarize some key advances field direct deoxy-borylation alcohols, ethers, aldehydes, ketones, carboxylic acids organize these contributions based on substrate classes. In each representative, general features, including reaction conditions, product scopes mechanistic insights, be highlighted discussed.

Язык: Английский

Molybdenum-catalyzed carbonyl–carbonyl olefination reaction for heterocycle syntheses DOI

Yuanqing Dong,

Xiao-Nan Shi,

Liya Cao

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(14), С. 3544 - 3552

Опубликована: Янв. 1, 2023

Here, we report a Mo-catalyzed carbonyl–carbonyl olefination reaction for the syntheses of several heterocycles, such as indoles, benzofurans, benzothiophene, 2-pyrone, coumarins and their derivatives.

Язык: Английский

Процитировано

8

Enantioselective α-C(sp3)–H Borylation of Masked Primary Alcohols Enabled by Iridium Catalysis DOI
Qian Gao, Yinwu Li, Lili Chen

и другие.

Journal of the American Chemical Society, Год журнала: 2024, Номер unknown

Опубликована: Дек. 18, 2024

Functional group-directed site- and enantioselective C(sp3)–H functionalization of alcohols or masked represents a formidable challenge. We herein report the first example iridium-catalyzed asymmetric α-C(sp3)–H borylation primary alcohol-derived carbamates by judicious choice directing groups. A variety chiral borylated were obtained with good to high enantioselectivities. also demonstrated synthetic utility taking advantage highly transformable feature C–B bonds leaving ability carbamates.

Язык: Английский

Процитировано

2

Recent advances in the chemistry of α-oxylboronate reagents DOI

Nan‐Quan Jiang,

Du Chen, Chao Liu

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(14), С. 3684 - 3700

Опубликована: Янв. 1, 2023

The synthesis and transformation of α-oxylboronates including their C–B bond C–O functionalizations are reviewed.

Язык: Английский

Процитировано

5

Formal Deoxygenative Cross‐Coupling of Aldehydes to Ketones through α‐Haloboronates: A Route to Deoxygenative Hydroacylation of Aldehydes DOI

Zihao Hu,

Wanqi Zhang, Tao Xu

и другие.

Chinese Journal of Chemistry, Год журнала: 2023, Номер 41(24), С. 3593 - 3597

Опубликована: Сен. 10, 2023

Comprehensive Summary Aldehydes are a kind of important synthons and reagents in organic synthesis. The efforts on transformations aldehydes highly rewarding have always attracted considerable attention. Herein, cross‐coupling with α‐haloboronates has been achieved under dual nickel/photoredox catalysis system. Considering the can be easily obtained from our deoxygenative difunctionalization carbonyls (DODC) strategy, this protocol provides formal to one‐carbon‐prolonged ketone products. mild conditions enabled good functional group tolerance broad substrate applicability. application method was presented via tunable synthesis two ketones very similar skeletons same aldehydes.

Язык: Английский

Процитировано

5

Influence of Cage Effects in Directing the Outcome of C–X Bond Forming Reactions DOI Creative Commons
Zihang Qiu, Constanze N. Neumann

ACS Organic & Inorganic Au, Год журнала: 2023, Номер 4(1), С. 1 - 25

Опубликована: Окт. 25, 2023

Radical reactions have recently experienced a resurgence in organic chemistry after many decades of being considered to be too unselective offer viable solution for complex synthetic problems. intermediates often number different reaction pathways available them that are all associated with insubstantial barriers so outcomes can controlled by proximity and dynamics. Cage effects consist the effect surrounding medium, such as solvent or enzyme pocket, on movement radical medium's resulting influence over selectivity. substantially affect outcome transformations condensed phases, which feature intermediacy pairs, suitable choice cage should thus constitute key optimization parameter reactions. This Perspective provides an overview aspects importance highlights its role reported forge C-X bonds via radicals.

Язык: Английский

Процитировано

5

Photoinduced radical addition process enables deoxygenative hydroacylation and hydrophosphonylation of carbonyls DOI Creative Commons
Xiaoqiang Wu, Jun Zhou,

Zihao Hu

и другие.

Chem Catalysis, Год журнала: 2023, Номер 4(1), С. 100828 - 100828

Опубликована: Дек. 4, 2023

Язык: Английский

Процитировано

3

Cross-coupling of aldehydes and α-bromophosphonates to modularly access α-substituted-β-ketophosphonates under dual nickel/photoredox catalysis DOI
Xinxuan Li,

Hepan Wang,

Tao Xu

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(12), С. 3061 - 3066

Опубликована: Янв. 1, 2023

β-Ketophosphonates are extremely valuable molecules in organic synthesis.

Язык: Английский

Процитировано

3

Deoxygenative Alkylboration of Aldehydes to Synthesize Versatile Secondary α,α-Dialkyl Boronates DOI
Liejin Zhou, Tao Xu,

Wenhao Xu

и другие.

Synlett, Год журнала: 2023, Номер 34(10), С. 1075 - 1078

Опубликована: Янв. 16, 2023

Abstract By merging nickel catalysis and photochemistry, we developed a deoxygenative alkylboration of aldehydes via difunctionalization carbonyls strategy. This three-component reaction between alkyl halides, B2Pin2, represents one the most efficient methods to furnish versatile secondary α,α-dialkyl boronates. A series skeletons can be gained from products based on carbon–boron bond transformation. In addition, arylboration was achieved.

Язык: Английский

Процитировано

2

Enantioconvergent Reductive C(sp)−C(sp3) Cross‐Coupling to Access Chiral α‐Alkynyl Phosphonates Under Dual Nickel/Photoredox Catalysis DOI

Hepan Wang,

Xiaoqiang Wu, Tao Xu

и другие.

Angewandte Chemie, Год журнала: 2023, Номер 135(18)

Опубликована: Март 8, 2023

Abstract Transition‐metal‐catalyzed asymmetric carbon−carbon bond formation to forge phosphonates with an α‐chiral carbon center through C(sp 3 )−C(sp ) and 2 couplings has been successful. However, the enantioselective C(sp)−C(sp coupling not yet disclosed. Reported herein is unprecedented enantioconvergent cross‐coupling of alkynyl bromides α‐bromo deliver chiral α‐alkynyl phosphonates.

Язык: Английский

Процитировано

1

Direct deoxygenative borylation DOI Creative Commons
Jianbin Li

Pure and Applied Chemistry, Год журнала: 2022, Номер 94(11-12), С. 1209 - 1224

Опубликована: Дек. 1, 2022

Abstract Direct deoxygenative borylation is a highly enabling chemical transformation considering the attractive synthetic features of oxygenous feedstocks and organoboron compounds. Despite ranking among ideality in different settings, such space remained largely uncharted underutilized until recent decades. This short review will summarize some key advances field direct deoxy-borylation alcohols, ethers, aldehydes, ketones, carboxylic acids organize these contributions based on substrate classes. In each representative, general features, including reaction conditions, product scopes mechanistic insights, be highlighted discussed.

Язык: Английский

Процитировано

2