Literature DB >> 33785969

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

Zhen Liu1, Yang Gao1, Tian Zeng2, Keary M Engle1.   

Abstract

During the past decade, many research groups have described catalytic methods for 1,2-carboboration, allowing access to structurally complex organoboronates from alkenes. Various transition metals, especially copper, palladium, and nickel, have been widely used in these reactions. This review summarizes advances in this field, with a special focus on the catalytic cycles involved in different metal-catalyzed carboboration reactions, as well as the regio- and stereochemical consequences of the underlying mechanisms. 1,2-Carboboration of other unsaturated systems, such as alkynes and allenes, are outside of the scope of this review.

Entities:  

Keywords:  1,2-Carboboration; Alkene; Catalysis; Mechanism; Transition-metal

Year:  2019        PMID: 33785969      PMCID: PMC8006804          DOI: 10.1002/ijch.201900087

Source DB:  PubMed          Journal:  Isr J Chem        ISSN: 0021-2148            Impact factor:   3.333


  66 in total

1.  Enantioselective 1,1-arylborylation of alkenes: merging chiral anion phase transfer with Pd catalysis.

Authors:  Hosea M Nelson; Brett D Williams; Javier Miró; F Dean Toste
Journal:  J Am Chem Soc       Date:  2015-02-27       Impact factor: 15.419

2.  Copper/palladium synergistic catalysis for the syn- and anti-selective carboboration of alkenes.

Authors:  Kaitlyn M Logan; Kevin B Smith; M Kevin Brown
Journal:  Angew Chem Int Ed Engl       Date:  2015-02-27       Impact factor: 15.336

3.  Copper-catalyzed cross-coupling of boronic esters with aryl iodides and application to the carboboration of alkynes and allenes.

Authors:  Yiqing Zhou; Wei You; Kevin B Smith; M Kevin Brown
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-24       Impact factor: 15.336

4.  Nickel-Catalyzed 1,2-Arylboration of Vinylarenes.

Authors:  Wang Wang; Chao Ding; Hailiang Pang; Guoyin Yin
Journal:  Org Lett       Date:  2019-05-10       Impact factor: 6.005

5.  Palladium-catalyzed, stereoselective, cyclizative alkenylboration of carbon-carbon double bonds through activation of a boron-chlorine bond.

Authors:  Masaki Daini; Michinori Suginome
Journal:  J Am Chem Soc       Date:  2011-03-10       Impact factor: 15.419

6.  Uncatalyzed Carboboration of Seven-Membered-Ring trans-Alkenes: Formation of Air-Stable Trialkylboranes.

Authors:  Jillian R Sanzone; Chunhua T Hu; K A Woerpel
Journal:  J Am Chem Soc       Date:  2017-06-16       Impact factor: 15.419

7.  Directed, Regiocontrolled Hydroamination of Unactivated Alkenes via Protodepalladation.

Authors:  John A Gurak; Kin S Yang; Zhen Liu; Keary M Engle
Journal:  J Am Chem Soc       Date:  2016-04-29       Impact factor: 15.419

8.  Copper-Catalyzed Heteroarylboration of 1,3-Dienes with 3-Bromopyridines: A cine Substitution.

Authors:  Kevin B Smith; Yuan Huang; M Kevin Brown
Journal:  Angew Chem Int Ed Engl       Date:  2018-04-26       Impact factor: 15.336

9.  Synthesis of optically active boron-silicon bifunctional cyclopropane derivatives through enantioselective copper(I)-catalyzed reaction of allylic carbonates with a diboron derivative.

Authors:  Hajime Ito; Yuki Kosaka; Kousuke Nonoyama; Yusuke Sasaki; Masaya Sawamura
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

10.  Palladium-Catalyzed Amide-Directed Enantioselective Hydrocarbofunctionalization of Unactivated Alkenes Using a Chiral Monodentate Oxazoline Ligand.

Authors:  Hao Wang; Zibo Bai; Tangqian Jiao; Zhiqiang Deng; Huarong Tong; Gang He; Qian Peng; Gong Chen
Journal:  J Am Chem Soc       Date:  2018-02-27       Impact factor: 15.419

View more
  5 in total

1.  Cooperative Pd/Cu Catalysis for Alkene Arylboration: Opportunities for Divergent Reactivity.

Authors:  Stanna K Dorn; M Kevin Brown
Journal:  ACS Catal       Date:  2022-01-24       Impact factor: 13.700

2.  Three-Component Ni-Catalyzed Silylacylation of Alkenes.

Authors:  Dongshun Ni; M Kevin Brown
Journal:  ACS Catal       Date:  2021-01-26       Impact factor: 13.700

Review 3.  1,2-Difunctionalizations of alkynes entailing concomitant C-C and C-N bond-forming carboamination reactions.

Authors:  Santosh Kumar Nanda; Rosy Mallik
Journal:  RSC Adv       Date:  2022-03-04       Impact factor: 3.361

4.  1,2-Carboboration of Arylallenes by In Situ Generated Alkenylboranes for the Synthesis of 1,4-Dienes.

Authors:  Arthur Averdunk; Max Hasenbeck; Tizian Müller; Jonathan Becker; Urs Gellrich
Journal:  Chemistry       Date:  2022-04-21       Impact factor: 5.020

5.  Construction of congested Csp3-Csp3 bonds by a formal Ni-catalyzed alkylboration.

Authors:  Amit Kumar Simlandy; Stephen R Sardini; M Kevin Brown
Journal:  Chem Sci       Date:  2021-03-09       Impact factor: 9.825

  5 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.