Literature DB >> 25846625

Organoborane catalyzed regioselective 1,4-hydroboration of pyridines.

Xiaoting Fan1, Junhao Zheng1, Zhen Hua Li1, Huadong Wang1.   

Abstract

A bulky organoborane Ar(F)2BMe (Ar(F) = 2,4,6-tris(trifluoromethyl)phenyl, 1) has been synthesized. In C6D6 solution this organoborane and pyridine form a frustrated Lewis pair. Under mild conditions, 1 can efficiently catalyze 1,4-hydroboration of a series of pyridines. This reaction is highly chemo- and regioselective. The reaction intermediate, a boronium complex [Py2Bpin][Ar(F)2B(H)Me] (3), was characterized in solution by NMR spectroscopy, which was also confirmed by DFT calculation.

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Year:  2015        PMID： 25846625     DOI： 10.1021/jacs.5b03147

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


  8 in total

1.  Evidence for Simultaneous Dearomatization of Two Aromatic Rings under Mild Conditions in Cu(I)-Catalyzed Direct Asymmetric Dearomatization of Pyridine.

Authors:  Michael W Gribble; Richard Y Liu; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2020-06-11       Impact factor: 15.419

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.  Asymmetric Cu-Catalyzed 1,4-Dearomatization of Pyridines and Pyridazines without Preactivation of the Heterocycle or Nucleophile.

Authors:  Michael W Gribble; Sheng Guo; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2018-04-06       Impact factor: 15.419

4.  1-Alkali-metal-2-alkyl-1,2-dihydropyridines: Soluble Hydride Surrogates for Catalytic Dehydrogenative Coupling and Hydroboration Applications.

Authors:  Ross McLellan; Alan R Kennedy; Robert E Mulvey; Samantha A Orr; Stuart D Robertson
Journal:  Chemistry       Date:  2017-11-03       Impact factor: 5.236

5.  N-Heterocycle-Ligated Borocations as Highly Tunable Carbon Lewis Acids.

Authors:  James E Radcliffe; Jay J Dunsford; Jessica Cid; Valerio Fasano; Michael J Ingleson
Journal:  Organometallics       Date:  2017-12-08       Impact factor: 3.876

6.  An umpolung approach to the hydroboration of pyridines: a novel and efficient synthesis of N-H 1,4-dihydropyridines.

Authors:  Huan Yang; Li Zhang; Fei-Yu Zhou; Lei Jiao
Journal:  Chem Sci       Date:  2019-12-03       Impact factor: 9.825

7.  Metal-free borylative dearomatization of indoles: exploring the divergent reactivity of aminoborane C-H borylation catalysts.

Authors:  Arumugam Jayaraman; Luis C Misal Castro; Vincent Desrosiers; Frédéric-Georges Fontaine
Journal:  Chem Sci       Date:  2018-05-07       Impact factor: 9.825

8.  Synthesis of cyclic chiral α-amino boronates by copper-catalyzed asymmetric dearomative borylation of indoles.

Authors:  Lili Chen; Jun-Jian Shen; Qian Gao; Senmiao Xu
Journal:  Chem Sci       Date:  2018-06-12       Impact factor: 9.825
  8 in total

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