Literature DB >> 17367156

Aminomethylations via cross-coupling of potassium organotrifluoroborates with aryl bromides.

Gary A Molander1, Deidre L Sandrock.   

Abstract

[reaction: see text] The Suzuki-Miyaura cross-coupling reaction of N,N-dialkylaminomethyltrifluoroborates with aryl halides allows the construction of an aminomethyl aryl linkage through a disconnection based on dissonant reactivity patterns. A variety of these aminomethyltrifluoroborate substrates were prepared in good to excellent yields and then shown to cross-couple with equal facility to both electron-rich and electron-poor aryl halides as well as to a variety of heteroaromatic bromides.

Entities:  

Mesh:

Substances:

Year:  2007        PMID: 17367156      PMCID: PMC2515366          DOI: 10.1021/ol070543e

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


  6 in total

1.  An extremely active catalyst for the Negishi cross-coupling reaction.

Authors:  Jacqueline E Milne; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2004-10-13       Impact factor: 15.419

Review 2.  Development of new synthetic methods and its application to total synthesis of nitrogen-containing bioactive natural products.

Authors:  Chihiro Kibayashi
Journal:  Chem Pharm Bull (Tokyo)       Date:  2005-11       Impact factor: 1.645

3.  Reductive Amination of Aldehydes and Ketones with Sodium Triacetoxyborohydride. Studies on Direct and Indirect Reductive Amination Procedures(1).

Authors:  Ahmed F. Abdel-Magid; Kenneth G. Carson; Bruce D. Harris; Cynthia A. Maryanoff; Rekha D. Shah
Journal:  J Org Chem       Date:  1996-05-31       Impact factor: 4.354

4.  Synthesis of an anti-methicillin-resistant Staphylococcus aureus (MRSA) carbapenem via stannatrane-mediated Stille coupling.

Authors:  M S Jensen; C Yang; Y Hsiao; N Rivera; K M Wells; J Y Chung; N Yasuda; D L Hughes; P J Reider
Journal:  Org Lett       Date:  2000-04-20       Impact factor: 6.005

5.  Catalysts for Suzuki-Miyaura coupling processes: scope and studies of the effect of ligand structure.

Authors:  Timothy E Barder; Shawn D Walker; Joseph R Martinelli; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2005-04-06       Impact factor: 15.419

6.  Synthesis of functionalized organotrifluoroborates via halomethyltrifluoroborates.

Authors:  Gary A Molander; Jungyeob Ham
Journal:  Org Lett       Date:  2006-05-11       Impact factor: 6.005

  6 in total
  17 in total

1.  Synthesis of amidomethyltrifluoroborates and their use in cross-coupling reactions.

Authors:  Gary A Molander; Marie-Aude Hiebel
Journal:  Org Lett       Date:  2010-11-05       Impact factor: 6.005

2.  Synthesis and Suzuki-Miyaura cross-coupling reactions of potassium Boc-protected aminomethyltrifluoroborate with aryl and hetaryl halides.

Authors:  Gary A Molander; Inji Shin
Journal:  Org Lett       Date:  2011-07-06       Impact factor: 6.005

3.  Discovery of AC710, a Globally Selective Inhibitor of Platelet-Derived Growth Factor Receptor-Family Kinases.

Authors:  Gang Liu; Brian T Campbell; Mark W Holladay; Julia M Ford Pulido; Helen Hua; Dana Gitnick; Michael F Gardner; Joyce James; Mike A Breider; Daniel Brigham; Barbara Belli; Robert C Armstrong; Daniel K Treiber
Journal:  ACS Med Chem Lett       Date:  2012-09-24       Impact factor: 4.345

4.  Synthesis and cross-coupling of sulfonamidomethyltrifluoroborates.

Authors:  Gary A Molander; Nicolas Fleury-Brégeot; Marie-Aude Hiebel
Journal:  Org Lett       Date:  2011-03-02       Impact factor: 6.005

5.  Suzuki-Miyaura cross-coupling of potassium trifluoro(N-methylheteroaryl)borates with aryl and heteroaryl halides.

Authors:  Gary A Molander; DaWeon Ryu; Mona Hosseini-Sarvari; Rammohan Devulapally; Dave G Seapy
Journal:  J Org Chem       Date:  2013-06-25       Impact factor: 4.354

6.  Aminomethylation of Aryl Halides using α-Silylamines Enabled by Ni/Photoredox Dual Catalysis.

Authors:  Camille Remeur; Christopher B Kelly; Niki R Patel; Gary A Molander
Journal:  ACS Catal       Date:  2017-08-16       Impact factor: 13.084

7.  Negishi coupling of secondary alkylzinc halides with aryl bromides and chlorides.

Authors:  Chong Han; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2009-06-10       Impact factor: 15.419

8.  Organotrifluoroborates and monocoordinated palladium complexes as catalysts--a perfect combination for Suzuki-Miyaura coupling.

Authors:  Gary A Molander; Belgin Canturk
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

Review 9.  Potassium trifluoroborate salts as convenient, stable reagents for difficult alkyl transfers.

Authors:  Gary A Molander; Deidre L Sandrock
Journal:  Curr Opin Drug Discov Devel       Date:  2009-11

10.  Preparation of potassium azidoaryltrifluoroborates and their cross-coupling with aryl halides.

Authors:  Young Ae Cho; Dong-Su Kim; Hong Ryul Ahn; Belgin Canturk; Gary A Molander; Jungyeob Ham
Journal:  Org Lett       Date:  2009-10-01       Impact factor: 6.005

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.