Recent Progress in Arylmetalative Cyclization/Annulation of Functionalized Alkynes with Organoboranes DOI
Manda Rajesh,

Gadi Ranjith Kumar

Asian Journal of Organic Chemistry, Год журнала: 2023, Номер 12(5)

Опубликована: Апрель 19, 2023

Abstract Achieving complex molecular assemblies in modular modes is always one of the top priorities organic chemist. Cyclization/annulation functionalized alkynes through carbo metalation has an impactful swath synthetic chemistry. There have recently been considerable contributions this arena uncovering several new chemical spaces towards solutions for various fields biology. On other hand, organoboronic reagents are fascinating reactive chemprobs, partake a broad range transformations. Particularly utility these carbo‐metalation subject high perusal To degree, tuning transition‐metal catalysts with organoboranes and intriguing synthesis classes acyclic cyclic adducts. Mechanistically, arylative cyclizations proceed initial aryl‐metalation on which provides alkenyl metal species, that concomitantly react pendent electrophile. The stereo‐ regioselective reactivity C‐metal steered by chelation coordinating group and/or electrophile alkyne. In review, we focused critical achievements field emphasis stereoselective capture vinyl field, compilation detailed mechanistic pathways realm would be helpful to find gaps hence discover novel

Язык: Английский

Rhodium(III)-Catalyzed Asymmetric Reductive Cyclization of Cyclohexadienone-Containing 1,6-Dienes via an Anti-Michael/Michael Cascade Process DOI
Hao Xu, Yun‐Xuan Tan, Pei‐Pei Xie

и другие.

ACS Catalysis, Год журнала: 2021, Номер 11(13), С. 8015 - 8022

Опубликована: Июнь 17, 2021

Ring strain plays an important role in metal-catalyzed cyclization of 1,6-dienes. Herein, we report a rhodium(III)-catalyzed asymmetric reductive cyclohexadienone-tethered α,β-unsaturated compounds (1,6-dienes), including ketones, esters, amides, sulfone, and phosphonate. The reactions undergo unusual anti-Michael/Michael addition process, affording cis-bicyclic frameworks with good to high yields diastereo- enantioselectivities. Furthermore, several transformations the products one-pot preparation bridged polycyclic structure are also presented. Finally, DFT calculations show that enantioselectivity is determined by initial olefin insertion step ring controls overall regioselectivity favors formation 5,6-bicyclic products.

Язык: Английский

Процитировано

17

Recent Advances in Nonprecious Metal Catalysis DOI
Robert A. Singer, Sébastien Monfette, David J. Bernhardson

и другие.

Organic Process Research & Development, Год журнала: 2021, Номер 25(8), С. 1802 - 1815

Опубликована: Авг. 10, 2021

Язык: Английский

Процитировано

17

Maleimide‐Controlled Formation of Indanonylpyrrolinediones and Spiroindanonylpyrrolinediones via Rh(III)‐Catalyzed C−H Activation of Sulfoxonium Ylides DOI
Perumal Muthuraja, Muhammad Saeed Akhtar, Purushothaman Gopinath

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(24), С. 4595 - 4602

Опубликована: Ноя. 1, 2023

Abstract A substrate‐controlled [4+1] annulation of sulfoxonium ylides with maleimides via Rh(III)‐catalyzed C−H bond activation is developed. The reaction 2‐methyl‐ N ‐arylmaleimides in the presence AgNTf 2 diastereoselectively provides diversely functionalized indanonylpyrroline‐2,5‐dione derivatives. Furthermore, AgBF 4 , subsequent leads to biologically intriguing various spiroindanonylpyrroline‐2,5‐diones. This methodology offers a broad substrate scope, good functional group tolerance, and diastereoselectivity.

Язык: Английский

Процитировано

7

Access to Benzocyclic Boronates via Light-Promoted Intramolecular Arylborylation of Alkenes DOI

Sen Ke,

Huanqing Liao,

Hao Qin

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(9), С. 6237 - 6246

Опубликована: Апрель 11, 2023

Benzocyclic boronates have attracted increasing research interest in drug chemistry and organic synthesis recent years. Herein, we report a facile access to benzocyclic through photopromoted intramolecular arylborylation of allyl aryldiazonium salts. This simple protocol features broad scope, allowing the formation variously functionalized borates bearing dihydrobenzofuran, dihydroindene, benzothiophene, indoline skeletons under mild sustainable conditions.

Язык: Английский

Процитировано

6

Recent Progress in Arylmetalative Cyclization/Annulation of Functionalized Alkynes with Organoboranes DOI
Manda Rajesh,

Gadi Ranjith Kumar

Asian Journal of Organic Chemistry, Год журнала: 2023, Номер 12(5)

Опубликована: Апрель 19, 2023

Abstract Achieving complex molecular assemblies in modular modes is always one of the top priorities organic chemist. Cyclization/annulation functionalized alkynes through carbo metalation has an impactful swath synthetic chemistry. There have recently been considerable contributions this arena uncovering several new chemical spaces towards solutions for various fields biology. On other hand, organoboronic reagents are fascinating reactive chemprobs, partake a broad range transformations. Particularly utility these carbo‐metalation subject high perusal To degree, tuning transition‐metal catalysts with organoboranes and intriguing synthesis classes acyclic cyclic adducts. Mechanistically, arylative cyclizations proceed initial aryl‐metalation on which provides alkenyl metal species, that concomitantly react pendent electrophile. The stereo‐ regioselective reactivity C‐metal steered by chelation coordinating group and/or electrophile alkyne. In review, we focused critical achievements field emphasis stereoselective capture vinyl field, compilation detailed mechanistic pathways realm would be helpful to find gaps hence discover novel

Язык: Английский

Процитировано

6