Pd-catalysed cross-coupling of allenylic carbonates with gem-diborylalkanes: efficient synthesis of isoprenylboronates DOI

Xin-Ru Ma,

Qin Zhong, Qiancheng Zhang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(16), P. 3355 - 3359

Published: Jan. 1, 2023

A simple and novel Pd-catalysed cross-coupling reaction of allenylic carbonates with different gem-diborylalkanes was developed. Under mild conditions, synthetically useful versatile isoprenylboronates could be obtained selectively in moderate to high yields. Furthermore, the utility isoprenylboronate is demonstrated through isoprenylboration homologation.

Language: Английский

Palladium‐Catalyzed Regioselective Domino Spirocyclization of Carbamoyl Chlorides with Alkynes and Benzynes DOI
Chenchen Wang,

Wenyu Zhao,

Xianqing Wu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2020, Volume and Issue: 362(22), P. 4996 - 5001

Published: Sept. 24, 2020

Abstract A palladium‐catalyzed domino spiro‐cyclization of carbamoyl chlorides with alkynes and benzynes, involving intramolecular C−H activation to afford valuable oxindole scaffolds bearing spiro quaternary stereocenters, has been developed. This one‐step synthesis spirooxindole is both step‐ atom‐economic, proceeding high regioselectivity in moderate excellent yields. magnified image

Language: Английский

Citations

22
Reactivity Trends with Borylalkyl Copper(I) Species DOI Creative Commons
Macarena Corro, Oriol Salvadó, Sara González

et al.

European Journal of Inorganic Chemistry, Journal Year: 2021, Volume and Issue: 2021(28), P. 2802 - 2813

Published: May 18, 2021

Abstract The renaissance on the application of gem ‐diborylalkanes from 2010, has allowed conquest new synthetic towards C−C and C−N bond formation. activation by Cu(I) catalysts, generates active borylalky copper(I) species that are able to trap several electrophilic reagents, in an efficient way. In addition, modification complexes with chiral ligands, induces asymmetric platforms synthesis enantioenriched organoboron compounds.

Language: Английский

Citations

18
Palladium-catalyzed synthesis of spirooxindoles and [3,4]-fused oxindoles from alkene-tethered carbamoyl chlorides DOI
Fang Yang,

Wan Sun,

Haifang Meng

et al.

Organic Chemistry Frontiers, Journal Year: 2020, Volume and Issue: 8(2), P. 283 - 287

Published: Nov. 23, 2020

We disclosed an efficient Pd-catalyzed domino reaction for the synthesis of spirooxindoles and [3,4]-fused oxindoles from alkene-tethered carbamoyl chlorides.

Language: Английский

Citations

19
Palladium-catalyzed domino Heck-disilylation and Heck-monosilylation of alkene-tethered carbamoyl chlorides: synthesis of versatile silylated oxindoles DOI
Chen Chen,

Wan Sun,

Liying Liu

et al.

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(10), P. 2250 - 2255

Published: Jan. 1, 2021

We report efficient domino Heck-disilylation and Heck-monosilylation of alkene-tethered carbamoyl chlorides with hexamethyldisilane under mild reaction conditions.

Language: Английский

Citations

16
Copper-catalyzed 1,6-conjugate addition of para-quinone methides with diborylmethane DOI
Xin Li,

Guoliang Gao,

Songtao He

et al.

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(16), P. 4543 - 4548

Published: Jan. 1, 2021

Presented herein is the first 1,6-conjugate addition of diborylmethane. This reaction features high yields, mild conditions, and broad functional group compatibilities.

Language: Английский

Citations

16
Mapping the Electronic Structure and the Reactivity Trends for Stabilized α‐Boryl Carbanions DOI
Ricardo J. Maza, Elena Fernández, Jorge J. Carbó

et al.

Chemistry - A European Journal, Journal Year: 2021, Volume and Issue: 27(48), P. 12352 - 12361

Published: June 22, 2021

Abstract The chemistry of stabilized α‐boryl carbanions shows remarkable diversity, and can enable many different synthetic routes towards efficient C−C bond formation. electron‐deficient, trivalent boron center stabilizes the carbanion facilitating its generation tuning reactivity. Here, electronic structure reactivity trends a large dataset are described. DFT‐derived parameters were used to capture their steric properties, computational model substrates, crystallographic analysis within Cambridge Structural Dataset. This study maps space by systematically varying nature boryl moiety, substituents carbanionic center, number motifs, metal counterion. In general, free intermediates described as borata‐alkene species with C−B π interactions polarized carbon. Furthermore, it was possible classify alkylidene precursors into three classes directly related reactivity: 1) nucleophilic salts alkali alkaline earth metals, 2) η 2 ‐(C−B) complexes early transition Cu Ag, 3) alkyl late metals. trend map aids selection appropriate reactive synthon depending on sought.

Language: Английский

Citations

13
Experimental and computational studies on the palladium-catalyzed intramolecular dearomatization, electrophilic addition, intermolecular coupling sequence DOI
Qinghui Liu, Yue Ma, Hong‐Yu Zhang

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 11(5), P. 1357 - 1365

Published: Dec. 28, 2023

An unprecedented Pd-catalyzed highly stereoselective synthetic strategy for the construction of a broad spectrum polycyclic fused indoline skeletons employing N -halobenzoyl o -haloanilines and -(prop-2-yn-1-yl)anilines as has been described.

Language: Английский

Citations

4
Synthesis of 1,1-Diboron Alkanes via Diborylation of Unactivated Primary C(sp3)—H Bonds Enabled by AsPh3/Iridium Catalysis DOI Open Access
Wenqi Liu, Zhenlu Shen, Senmiao Xu

et al.

Chinese Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 42(4), P. 1101 - 1101

Published: Jan. 1, 2022

The AsPh3/iridium catalyzed diborylation of unactivated primary C(sp 3 )-H bonds using pyrazoles as directing groups was disclosed.This method could tolerate a variety functional groups, affording vast array 1,1-diboron alkanes in moderate to good yields.The synthetic utility the current on gram-scale reaction for further functionalization also demonstrated.

Language: Английский

Citations

7
Enantioselective Carbonylative Cyclization of Alkenes with C–H Bonds for Synthesis of γ-Lactams Bearing an α-Quaternary Carbon DOI
Weiwei Xu, Yanan Sun,

Yuqing Jiang

et al.

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 19, 2024

The development of effective synthetic methods to construct γ-lactams bearing a chiral α-quaternary carbon from relatively inert C(O)–H bonds with alkenes has been an elusive challenge. Herein, we used naphthylamine-derived phosphine oxide ligating Ni and Al bimetallic catalyst realize carbonylative cyclization formyl C–H alkenes, highly regio- enantioselectively constructing in up 99% yield 98% ee. These proved be versatile precursors for many biologically active molecules.

Language: Английский

Citations

1
Palladium‐Catalyzed Carbamoyl‐Carbamoylation/ Carboxylation/Thioesterification of Alkene‐Tethered Carbamoyl Chlorides Using Mo(CO)6 as the Carbonyl Source DOI
Chen Chen, Yujie Huang, Jie Ding

et al.

Advanced Synthesis & Catalysis, Journal Year: 2021, Volume and Issue: 364(4), P. 794 - 801

Published: Dec. 16, 2021

Abstract We reported a palladium‐catalyzed carbamoyl‐carbamoylation/carboxylation/thioesterification of alkene‐tethered carbamoyl chlorides using Mo(CO) 6 as the carbonyl source. The reactions were typically performed with good functional group compatibility and tolerated different nucleophiles (amines, alcohols, phenols, thiols water), which provided new access to amidated/esterificated/thioesterificated/carboxylated oxindoles or lactams bearing an all‐carbon quaternary stereocenter under CO gas‐free conditions. Furthermore, natural product mutation divergent late‐stage derivatization are important practical features. magnified image

Language: Английский

Citations

9