Literature DB >> 22135233

Alkylboronic esters from copper-catalyzed borylation of primary and secondary alkyl halides and pseudohalides.

Chu-Ting Yang1, Zhen-Qi Zhang, Hazmi Tajuddin, Chen-Cheng Wu, Jun Liang, Jing-Hui Liu, Yao Fu, Maria Czyzewska, Patrick G Steel, Todd B Marder, Lei Liu.   

Abstract

Easy access: An unprecedented copper-catalyzed cross-coupling reaction of the title compounds with diboron reagents is described (see scheme; Ts = 4-toluenesulfonyl). This reaction can be used to prepare both primary and secondary alkylboronic esters having diverse structures and functional groups. The resulting products would be difficult to access by other means.
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2011        PMID： 22135233     DOI： 10.1002/anie.201106299

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  48 in total

1.  Nickel-catalyzed coupling reactions of alkyl electrophiles, including unactivated tertiary halides, to generate carbon-boron bonds.

Authors:  Alexander S Dudnik; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2012-06-06       Impact factor: 15.419

2.  Palladium-catalyzed borylation of primary alkyl bromides.

Authors:  Amruta Joshi-Pangu; Xinghua Ma; Mohamed Diane; Sidra Iqbal; Robert J Kribs; Richard Huang; Chao-Yuan Wang; Mark R Biscoe
Journal:  J Org Chem       Date:  2012-07-23       Impact factor: 4.354

3.  Decarboxylative borylation.

Authors:  Chao Li; Jie Wang; Lisa M Barton; Shan Yu; Maoqun Tian; David S Peters; Manoj Kumar; Antony W Yu; Kristen A Johnson; Arnab K Chatterjee; Ming Yan; Phil S Baran
Journal:  Science       Date:  2017-04-13       Impact factor: 47.728

4.  Synthesis and applications of α-trifluoromethylated alkylboron compounds.

Authors:  O Andreea Argintaru; DaWeon Ryu; Ioana Aron; Gary A Molander
Journal:  Angew Chem Int Ed Engl       Date:  2013-11-07       Impact factor: 15.336

5.  Transition-Metal-Catalyzed 1,2-Carboboration of Alkenes: Strategies, Mechanisms, and Stereocontrol.

Authors:  Zhen Liu; Yang Gao; Tian Zeng; Keary M Engle
Journal:  Isr J Chem       Date:  2019-09-10       Impact factor: 3.333

6.  Benzyltriboronates: Building Blocks for Diastereoselective Carbon-Carbon Bond Formation.

Authors:  W Neil Palmer; Cayetana Zarate; Paul J Chirik
Journal:  J Am Chem Soc       Date:  2017-02-13       Impact factor: 15.419

7.  Asymmetric synthesis: cascades of catalytic selectivity.

Authors:  Rian D Dewhurst; Todd B Marder
Journal:  Nat Chem       Date:  2014-04       Impact factor: 24.427

8.  Exhaustive Suzuki-Miyaura reactions of polyhalogenated heteroarenes with alkyl boronic pinacol esters.

Authors:  Sébastien Laulhé; J Miles Blackburn; Jennifer L Roizen
Journal:  Chem Commun (Camb)       Date:  2017-06-29       Impact factor: 6.222

9.  Sterically Unprotected Nucleophilic Boron Cluster Reagents.

Authors:  Xin Mu; Jonathan C Axtell; Nicholas A Bernier; Kent O Kirlikovali; Dahee Jung; Alexander Umanzor; Kevin Qian; Xiangyang Chen; Katherine L Bay; Monica Kirollos; Arnold L Rheingold; K N Houk; Alexander M Spokoyny
Journal:  Chem       Date:  2019-08-22       Impact factor: 22.804

10.  Suzuki-Miyaura cross-coupling of potassium dioxolanylethyltrifluoroborate and aryl/heteroaryl chlorides.

Authors:  Nicolas Fleury-Brégeot; Daniel Oehlrich; Frederik Rombouts; Gary A Molander
Journal:  Org Lett       Date:  2013-03-14       Impact factor: 6.005
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