BF3 Mediated [1,5]‐Hydride Shift Triggered Cyclization: Thioethers Join the Game DOI
Elvira R. Zaitseva, Alexander Yu. Smirnov, Vladimir I. Timashev

и другие.

European Journal of Organic Chemistry, Год журнала: 2022, Номер 2022(25)

Опубликована: Май 19, 2022

Abstract 2‐(2‐(Benzylthio)benzylidene)malonates can undergo the 1,5‐hydride shift triggered cyclization resulting in thiachromanes 45–84 % yield. Boron trifluoride as a reaction promotor is key to success. DFT calculations revealed that proceeds via chelate BF2 complex, which was confirmed by NMR‐analysis. Experimental and theoretical comparison of nitrogen, sulfur carbon analogues derivatives have highest activation barrier for hydride transfer due unfavorable transition state geometry, explains lack previous reports on shifts (alkylthio)styrenes.

Язык: Английский

Recent advances in hydride transfer-involved C(sp3)–H activation reactions DOI
Xiao‐De An, Jian Xiao

Organic Chemistry Frontiers, Год журнала: 2021, Номер 8(6), С. 1364 - 1383

Опубликована: Янв. 1, 2021

This review summarizes the recent progresses (2016–2020) in hydride transfer-enabled C(sp3)–H activation according to reaction types, categorized into intramolecular/intermolecular functionalization, and reduction.

Язык: Английский

Процитировано

88

Merging dearomatization with redox-neutral C(sp3)–H functionalization via hydride transfer/cyclization: recent advances and perspectives DOI
Fangzhi Hu, Yao‐Bin Shen, Liang Wang

и другие.

Organic Chemistry Frontiers, Год журнала: 2022, Номер 9(18), С. 5041 - 5052

Опубликована: Янв. 1, 2022

This review highlights the encouraging advances in hydride transfer-involved dearomatization reaction during past decade, content of which is categorized according to acceptors, namely vinylogous imines and quinone methides.

Язык: Английский

Процитировано

35

Hydride transfer enabled switchable dearomatization of indoles in the carbocyclic ring and the pyrrole ring DOI

Kang Duan,

Hongjin Shi,

Lin-Xuan Wang

и другие.

Organic Chemistry Frontiers, Год журнала: 2020, Номер 7(17), С. 2511 - 2517

Опубликована: Янв. 1, 2020

Hydride transfer enabled the first success of regioselective dearomatization indoles in carbocyclic ring and pyrrole ring, which was induced by ortho-quinone methides vinylogous iminium intermediates, respectively.

Язык: Английский

Процитировано

43

C(sp3)–H Bond Functionalization Mediated by Hydride a Shift/Cyclization System DOI
Keiji Mori

Bulletin of the Chemical Society of Japan, Год журнала: 2022, Номер 95(2), С. 296 - 305

Опубликована: Янв. 12, 2022

Abstract An efficient catalytic internal redox reaction (hydride shift mediated C(sp3)–H bond functionalization) has been developed, which the following salient features: (1) functionalization, (2) Lewis and/or Brønsted acid catalyzed (transition metals employed in conventional C–H functionalization are not required), and (3) construction of complex polycycles that otherwise difficult to synthesize by methods. Our recent efforts on development novel types hydride shift/cyclization system described.

Язык: Английский

Процитировано

26

Hydride Transfer-Initiated Cross-Dehydrogenative Coupling Reaction to Access Nine-Membered Rings DOI
Xiao‐De An,

Da-Ying Shao,

Bin Qiu

и другие.

Organic Letters, Год журнала: 2023, Номер 25(14), С. 2432 - 2437

Опубликована: Апрель 5, 2023

An unprecedented hydride transfer-triggered cross-dehydrogenative coupling of two C(sp3)-H bonds to target nine-membered rings has been developed. Salient features this methodology include atom and step economy metal-free redox-neutral conditions, with water as the byproduct proceeding well even decomposed aldehydes.

Язык: Английский

Процитировано

17

Organocatalytic cascade aldimine condensation/[1,6]-hydride transfer/Mannich-type cyclization: sustainable access to indole-2,3-fused diazocanes DOI

Lin-Xuan Wang,

Bin Qiu, Xiao‐De An

и другие.

Green Chemistry, Год журнала: 2021, Номер 23(20), С. 8181 - 8186

Опубликована: Янв. 1, 2021

An unprecedented organocatalytic cascade aldimine condensation/[1,6]-hydride transfer/Mannich-type cyclization of indole-2-carbaldehydes with o -aminoanilines was developed to assemble indole-2,3-fused diazocanes in one step.

Язык: Английский

Процитировано

32

Alkyl amines and ethers as traceless hydride donors in [1,5]-hydride transfer cascade reactions DOI
Yao‐Bin Shen, Fangzhi Hu, Shuai‐Shuai Li

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(4), С. 700 - 714

Опубликована: Янв. 1, 2023

The use of alkyl amines and ethers as traceless hydride donors in [1,5]-hydride transfer cascade reactions has been reviewed herein.

Язык: Английский

Процитировано

13

Switchable Synthesis of Spirodihydroindolizines and Indolizines from Aurones and Pyridin-2-yl Active Methylene Compounds DOI
Quan Liu, Feng Wang,

Zeng‐Yang He

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(3), С. 1753 - 1761

Опубликована: Янв. 22, 2024

A novel and flexible domino reaction of aurones with pyridin-2-yl active methylene compounds promoted by I2/BF3 has been developed to afford spirodihydroindolizines indolizines in a controllable manner. When the was performed 1,2-dichloroethane at 80 °C, variety were obtained, whereas it almost exclusively provided series when mixed solvent N,N-dimethylformamide relatively higher temperature 100 °C. Being metal-free, excellent product selectivity, high atom economy, good functional group tolerance, feasibility for large-scale synthesis are salient features methodology.

Язык: Английский

Процитировано

5

Access to Polycyclic Indole-3,4-Fused Nine-Membered Ring via Cascade 1,6-Hydride Transfer/Cyclization DOI
Shuo Yang, Xiao‐De An, Bin Qiu

и другие.

Organic Letters, Год журнала: 2021, Номер 23(23), С. 9100 - 9105

Опубликована: Ноя. 12, 2021

A cascade aldimine condensation/1,6-hydride transfer/Mannich-type cyclization of indole-derived phenylenediamine with aldehydes was developed for one-step construction a polycyclic indole-3,4-fused skeleton. Aldehyde serves as key to start the whole process, including 1,6-hydride transfer enabled δ-C(sp3)–H activation secondary amine. The challenges medium-sized rings are addressed via hydride chemistry.

Язык: Английский

Процитировано

24

An Intramolecular Nitroso-Meerwein–Ponndorf–Verley–Oppenauer Reaction to Access Fused Pyrrolidine Scaffolds DOI
Roman S. Malykhin, Svetlana A. Aksenova, Alexey Yu. Sukhorukov

и другие.

Organic Letters, Год журнала: 2024, Номер 26(2), С. 450 - 455

Опубликована: Янв. 8, 2024

δ-Hydroxy chloronitroso compounds generated in situ from 1,2-oxazine N-oxides undergo a 1,5-hydride transfer related to the Meerwein–Ponndorf–Verley–Oppenauer reaction. Based on process discovered, three-step access fused pyrrolidine scaffolds containing up four contiguous stereogenic centers starting simple nitrostyrenes and cycloalkenes or cyclodienes has been developed. The suggested reaction mechanism was confirmed by UV–vis ATR FT-IR monitoring DFT calculations.

Язык: Английский

Процитировано

4