Literature DB >> 22946740

Regioselective catalytic hydroboration of propargylic species using Cu(I)-NHC complexes.

Jin Kyoon Park1, Brian A Ondrusek, D Tyler McQuade.   

Abstract

The catalytic regioselective hydroboration of propargylic alcohols and ethers was investigated using NHC-CuCl. We observe that different NHC-CuCl complexes catalyze hydroborations of propargylic substrates with opposite regioselectivity. A 6-NHC-CuCl complex provides α-selectivity whereas β-selectivity is achieved using a 5-NHC-CuCl complex. The reaction tolerates a wide range of functional groups.

Entities:  

Mesh：

Substances：

Year:  2012        PMID： 22946740     DOI： 10.1021/ol302086v

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  9 in total

1.  Enantioselective synthesis of boron-substituted quaternary carbon stereogenic centers through NHC-catalyzed conjugate additions of (pinacolato)boron units to enones.

Authors:  Suttipol Radomkit; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2014-02-24       Impact factor: 15.336

2.  NHC-Cu-catalyzed protoboration of monosubstituted allenes. Ligand-controlled site selectivity, application to synthesis and mechanism.

Authors:  Fanke Meng; Byunghyuck Jung; Fredrik Haeffner; Amir H Hoveyda
Journal:  Org Lett       Date:  2013-03-05       Impact factor: 6.005

3.  Palladium-catalyzed chemoselective allylic substitution, Suzuki-Miyaura cross-coupling, and allene formation of bifunctional 2-B(pin)-substituted allylic acetate derivatives.

Authors:  Byeong-Seon Kim; Mahmud M Hussain; Nusrah Hussain; Patrick J Walsh
Journal:  Chemistry       Date:  2014-07-30       Impact factor: 5.236

4.  Regiocontrol in catalytic reductive couplings through alterations of silane rate dependence.

Authors:  Evan P Jackson; John Montgomery
Journal:  J Am Chem Soc       Date:  2015-01-05       Impact factor: 15.419

5.  Intercepting the Gold-Catalysed Meyer-Schuster Rearrangement by Controlled Protodemetallation: A Regioselective Hydration of Propargylic Alcohols.

Authors:  Matthew N Pennell; Michael P Kyle; Samantha M Gibson; Louise Male; Peter G Turner; Richard S Grainger; Tom D Sheppard
Journal:  Adv Synth Catal       Date:  2016-04-27       Impact factor: 5.837

6.  Synthesis of the C1-C27 Fragment of Stambomycin D Validates Modular Polyketide Synthase-Based Stereochemical Assignments.

Authors:  Jieyan Lim; Venkaiah Chintalapudi; Haraldur G Gudmundsson; Minh Tran; Alice Bernasconi; Araceli Blanco; Lijiang Song; Gregory L Challis; Edward A Anderson
Journal:  Org Lett       Date:  2021-09-08       Impact factor: 6.005

7.  Copper-catalyzed radical trans-selective hydroboration of ynamides with N-heterocyclic carbene boranes.

Authors:  Kefeng Wang; Qingzhen Yu; Wenli Mao; Yuxin Zheng; Jing Xu; Yukun Wang
Journal:  iScience       Date:  2022-08-17

8.  Mechanistic Insights into Carbonyl-Directed Rhodium-Catalyzed Hydroboration: ab Initio Study of a Cyclic γ,δ-Unsaturated Amide.

Authors:  Zhao-Di Yang; Rhitankar Pal; Gia L Hoang; Xiao Cheng Zeng; James M Takacs
Journal:  ACS Catal       Date:  2014-01-22       Impact factor: 13.084

9.  A broadly applicable NHC-Cu-catalyzed approach for efficient, site-, and enantioselective coupling of readily accessible (pinacolato)alkenylboron compounds to allylic phosphates and applications to natural product synthesis.

Authors:  Fang Gao; James L Carr; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2014-01-28       Impact factor: 15.419
  9 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.