Literature DB >> 25412033

Boron-catalyzed silylative reduction of quinolines: selective sp3 C-Si bond formation.

Narasimhulu Gandhamsetty1, Seewon Joung, Sung-Woo Park, Sehoon Park, Sukbok Chang.   

Abstract

A silylative reduction of quinolines to synthetically versatile tetrahydroquinoline molecules involving the formation of a C(sp(3))-Si bond exclusively β to nitrogen is described. Triarylborane is a highly efficient catalyst (up to 1000 turnovers), and silanes serve as both a silyl source and a reducing reagent. The present procedure is convenient to perform even on a large scale with excellent stereoselectivity. Mechanistic studies revealed that the formation of a 1,4-addition adduct is rate-limiting while the subsequent C(sp(3))-Si bond-forming step from the 1,4-adduct is facile.

Entities:  

Year:  2014        PMID： 25412033     DOI： 10.1021/ja510674u

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  7 in total

1.  β-Hydroxy-tetrahydroquinolines from Quinolines Using Chloroborane: Synthesis of the Peptidomimetic FISLE-412.

Authors:  Ahmad S Altiti; Kai Fan Cheng; Mingzhu He; Yousef Al-Abed
Journal:  Chemistry       Date:  2017-07-26       Impact factor: 5.236

Review 2.  Activation of Si-H and B-H bonds by Lewis acidic transition metals and p-block elements: same, but different.

Authors:  Pablo Ríos; Amor Rodríguez; Salvador Conejero
Journal:  Chem Sci       Date:  2022-06-06       Impact factor: 9.969

3.  Borane catalysed ring opening and closing cascades of furans leading to silicon functionalized synthetic intermediates.

Authors:  Chinmoy K Hazra; Narasimhulu Gandhamsetty; Sehoon Park; Sukbok Chang
Journal:  Nat Commun       Date:  2016-11-28       Impact factor: 14.919

4.  Silylation of Pyridine, Picolines, and Quinoline with a Zinc Catalyst.

Authors:  Joshua W Prybil; Rodney Wallace; Alexandra Warren; Jordan Klingman; Romane Vaillant; Michael B Hall; Xin Yang; William W Brennessel; Robert M Chin
Journal:  ACS Omega       Date:  2020-01-10

5.  Borane-catalyzed cascade Friedel-Crafts alkylation/[1,5]-hydride transfer/Mannich cyclization to afford tetrahydroquinolines.

Authors:  Bei-Bei Zhang; Shuo Peng; Feiyi Wang; Cuifen Lu; Junqi Nie; Zuxing Chen; Guichun Yang; Chao Ma
Journal:  Chem Sci       Date:  2021-12-20       Impact factor: 9.825

6.  Synthesis of Cyclic N-Acyl Amidines by [3 + 2] Cycloaddition of N-Silyl Enamines and Activated Acyl Azides.

Authors:  Dong Geun Jo; Changeun Kim; Sinjae Lee; Sooyeon Yun; Seewon Joung
Journal:  Molecules       Date:  2022-03-04       Impact factor: 4.411

7.  Controlled partial transfer hydrogenation of quinolines by cobalt-amido cooperative catalysis.

Authors:  Maofu Pang; Jia-Yi Chen; Shengjie Zhang; Rong-Zhen Liao; Chen-Ho Tung; Wenguang Wang
Journal:  Nat Commun       Date:  2020-03-06       Impact factor: 14.919
  7 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.