Dong‐Hang Tan

Catalytic enantioselective synthesis of alkylidenecyclopropanes

Jonathan C. Golec, Dong‐Hang Tan, Ken Yamazaki, Eveline H. Tiekink et autres

Abstract The enantioselective construction of small-ring carbocycles provides organic chemists with an enduring challenge1. Despite their commercial importance, enantioselective synthetic routes towards alkylidenecyclopropanes, a class of small-ring carbocycles, remain underdeveloped2,3. Alkylidenecyclopropanes can be converted into cyclopropanes, a common feature in drug molecules …

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Cp∗Rh(III)-catalyzed enantioselective C(sp3)–H amidation of azine-linked cyclobutanes

Xing Xu, Heyao Shi, Dong‐Hang Tan, Phillip Biallas et autres

The highly enantioselective desymmetrizing C(sp 3 )–H amidation of azine-linked cyclobutanes with dioxazolones to afford enantioenriched cis -configured amido-substituted pyrimidylcyclobutane scaffolds is described. The reaction is catalyzed by an electron-deficient Cp∗Rh(III) complex in combination with a novel axially chiral carboxylic acid that …

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Nickel-Catalyzed Reductive Decarboxylative/Deaminative Glycosylation of Activated Aliphatic Acids and Primary Amines

Xu‐Ge Liu, Qian Yang, Deng-Yin Liu, Jing Liu et autres

This study describes the nickel-catalyzed reductive decarboxylative/deaminative glycosylation of activated aliphatic acids/amines. Various alkyl C -glycosides were efficiently constructed under simple and mild reaction conditions. The reactions were high-yielding and exhibited a broad substrate scope, thereby enabling the transformation of some structurally …

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Deaminative bromination, chlorination, and iodination of primary amines

Jiang‐Hao Xue, Yin Li, Dong‐Hang Tan, Fang‐Hai Tu et autres

The primary amino group has been seldom utilized as a transformable functionality in organic synthesis. Reported herein is a deaminative halogenation of primary amines using N -anomeric amide as the nitrogen-deletion reagent. Both aliphatic and aromatic amines are competent substrates for direct …

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Synthesis of β-tosyloxylated gem-difluoroalkanes via sulfonyloxy migration

Fang‐Hai Tu, Yi Wang, Zhan Li, Shuang Yang et autres

gem -Difluoroalkanes widely exist in pharmaceuticals, agrochemicals, and materials. The synthesis of gem -difluoroalkane synthons bearing a latent functional group is of significant value but is rarely explored. Reported herein is a facile synthesis of tosyloxylated gem -difluoroalkanes via an oxidative fluorination …

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Synthesis of -Tosyloxylated gem-Difluoroalkanes via Elusive [2,3]-Sulfonyloxy Migration

Honggen Wang, Fang‐Hai Tu, Yi Wang, Zhan Li et autres

gem-Difluoroalkanes widely exist in pharmaceuticals, agrochemicals and materials. Reported herein is a facile synthesis of tosyloxylated gem-difluoroalkanes via an oxidative fluorination of readily available vinyl sulfonates. An intriguing [2,3]-sulfonyloxy migration, which has been rarely known, is involved as a key step. The …

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Synthesis of -Tosyloxylated gem-Difluoroalkanes via Oxidative Fluorination of Vinyl Sulfonates Featuring A [2,3]-Sulfonyloxy Migration

Honggen Wang, Fang‐Hai Tu, Zhan Li, Shuang Yang et autres

The gem-difluoroalkanes widely exist in pharmaceuticals, agrochemicals and materials. Reported herein is a facile synthesis of tosyloxylated gem-difluoroalkanes via an oxidative fluorination of readily available vinyl sulfonates. An intriguing [2,3]-sulfonyloxy migration is involved as a key step. The OTs group in the …

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A boryl-migratory semipinacol rearrangement

Dong‐Hang Tan, Ling Yang, Chang-Ting Li, Fang‐Hai Tu et autres

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Hypervalent iodine-mediated β-difluoroalkylboron synthesis via an unusual 1,2-hydrogen shift enabled by boron substitution

Wen‐Xin Lv, Yin Li, Yuan‐Hong Cai, Dong‐Hang Tan et autres

-methyliminodiacetyl) boronate (BMIDA) motif is responsible for the high regio- and chemoselectivity. The protocol provides facile access to a broad range of β-difluoroalkylborons under rather mild conditions. The value of these products was demonstrated by further transformations of the boryl group into …

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Regiocontrolled allylic functionalization of internal alkene via selenium-π-acid catalysis guided by boron substitution

Ling Yang, Yuan Liu, Wenxin Fan, Dong‐Hang Tan et autres

The selenium-π-acid-catalysis has received increasing attention as a powerful tool for olefin functionalization, but the regioselectivity is often problematic. Reported herein is a selenium-catalyzed regiocontrolled olefin transpositional chlorination and imidation reaction. The reaction outcome benefits from an allylic B(MIDA) substitution. And the …

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Synthesis of -Tosyloxylated gem-Difluoroalkanes via Oxidative Fluorination of Vinyl Sulfonates Featuring A [2,3]-Sulfonyloxy Migration

Honggen Wang, Fang‐Hai Tu, Li Zhan, Shuang Yang et autres

The gem-difluoroalkanes widely exist in pharmaceuticals, agrochemicals and materials. Reported herein is a facile synthesis of tosyloxylated gem-difluoroalkanes via an oxidative fluorination of readily available vinyl sulfonates. An intriguing [2,3]-sulfonyloxy migration is involved as a key step. The OTs group in the …

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Regiocontrolled Allylic Functionalization of Internal Alkene via Selenium-pi-Acid Catalysis Guided by Boron Substitution

Honggen Wang, Ling Yang, Yuan Liu, Wen‐Xin Fan et autres

The selenium-pi-acid-catalysis has received increasing attention as powerful tools for olefin functionalization, but the regioselectivity is often problematic. Reported herein is a selenium-catalyzed regiocontrolled olefin transpositional chlorination and imidation reaction. The reaction outcome benefits from an allylic B(MIDA) substitution. And the stabilization …

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