Metal-Free Borane-Catalyzed Highly Stereoselective Hydrogenation of Pyridines

A metal-free direct hydrogenation of pyridines was successfully realized by using homogeneous borane catalysts generated from alkenes and HB(C6F5)2 via in situ hydroboration. The reaction affords a broad range of piperidines in high yields with excellent cis stereoselectivities.

Saved in:
Bibliographic Details
Published in:Journal of the American Chemical Society 2013-09, Vol.135 (35), p.12968-12971
Main Authors: Liu, Yongbing, Du, Haifeng
Format: Article
Language:English
Subjects:
Boranes - chemistry
Catalysis
Hydrogenation
Molecular Structure
Piperidines - chemical synthesis
Piperidines - chemistry
Pyridines - chemistry
Stereoisomerism
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-a381t-a8cadd0521da07788ba03e5f801b00872f4d9de64cae6d0aa8b569894317b3013
cites cdi_FETCH-LOGICAL-a381t-a8cadd0521da07788ba03e5f801b00872f4d9de64cae6d0aa8b569894317b3013
container_end_page 12971
container_issue 35
container_start_page 12968
container_title Journal of the American Chemical Society
container_volume 135
creator Liu, Yongbing
Du, Haifeng
description A metal-free direct hydrogenation of pyridines was successfully realized by using homogeneous borane catalysts generated from alkenes and HB(C6F5)2 via in situ hydroboration. The reaction affords a broad range of piperidines in high yields with excellent cis stereoselectivities.
doi_str_mv 10.1021/ja406761j
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1430397411</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1430397411</sourcerecordid><originalsourceid>FETCH-LOGICAL-a381t-a8cadd0521da07788ba03e5f801b00872f4d9de64cae6d0aa8b569894317b3013</originalsourceid><addsrcrecordid>eNptkE1Lw0AQhhdRbP04-AckF0EP0dnsJtkctVgrtCio5zDJTmpCmq27iRB_vSmtPXka3uHhZeZh7ILDLYeA31UoIYojXh2wMQ8D8EMeRIdsDACBH6tIjNiJc9UQZaD4MRsFIpFSKDFmiwW1WPtTS-Q9GIsN-RMcNv0PaW9WLj_r3ntryZJxVFPelt_kzXptzZIabEvTeKbwXntb6rIhd8aOCqwdne_mKfuYPr5PZv785el5cj_3USje-qhy1BrCgGuEOFYqQxAUFgp4BqDioJA60RTJHCnSgKiyMEpUIgWPMwFcnLLrbe_amq-OXJuuSpdTXQ_3m86lXAoQSSz5Br3Zork1zlkq0rUtV2j7lEO6sZfu7Q3s5a62y1ak9-SfrgG42gKYu7QynW2GL_8p-gUWVnXB</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1430397411</pqid></control><display><type>article</type><title>Metal-Free Borane-Catalyzed Highly Stereoselective Hydrogenation of Pyridines</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read &amp; Publish Agreement 2022-2024 (Reading list)</source><creator>Liu, Yongbing ; Du, Haifeng</creator><creatorcontrib>Liu, Yongbing ; Du, Haifeng</creatorcontrib><description>A metal-free direct hydrogenation of pyridines was successfully realized by using homogeneous borane catalysts generated from alkenes and HB(C6F5)2 via in situ hydroboration. The reaction affords a broad range of piperidines in high yields with excellent cis stereoselectivities.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja406761j</identifier><identifier>PMID: 23944383</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Boranes - chemistry ; Catalysis ; Hydrogenation ; Molecular Structure ; Piperidines - chemical synthesis ; Piperidines - chemistry ; Pyridines - chemistry ; Stereoisomerism</subject><ispartof>Journal of the American Chemical Society, 2013-09, Vol.135 (35), p.12968-12971</ispartof><rights>Copyright © 2013 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a381t-a8cadd0521da07788ba03e5f801b00872f4d9de64cae6d0aa8b569894317b3013</citedby><cites>FETCH-LOGICAL-a381t-a8cadd0521da07788ba03e5f801b00872f4d9de64cae6d0aa8b569894317b3013</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23944383$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Liu, Yongbing</creatorcontrib><creatorcontrib>Du, Haifeng</creatorcontrib><title>Metal-Free Borane-Catalyzed Highly Stereoselective Hydrogenation of Pyridines</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>A metal-free direct hydrogenation of pyridines was successfully realized by using homogeneous borane catalysts generated from alkenes and HB(C6F5)2 via in situ hydroboration. The reaction affords a broad range of piperidines in high yields with excellent cis stereoselectivities.</description><subject>Boranes - chemistry</subject><subject>Catalysis</subject><subject>Hydrogenation</subject><subject>Molecular Structure</subject><subject>Piperidines - chemical synthesis</subject><subject>Piperidines - chemistry</subject><subject>Pyridines - chemistry</subject><subject>Stereoisomerism</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNptkE1Lw0AQhhdRbP04-AckF0EP0dnsJtkctVgrtCio5zDJTmpCmq27iRB_vSmtPXka3uHhZeZh7ILDLYeA31UoIYojXh2wMQ8D8EMeRIdsDACBH6tIjNiJc9UQZaD4MRsFIpFSKDFmiwW1WPtTS-Q9GIsN-RMcNv0PaW9WLj_r3ntryZJxVFPelt_kzXptzZIabEvTeKbwXntb6rIhd8aOCqwdne_mKfuYPr5PZv785el5cj_3USje-qhy1BrCgGuEOFYqQxAUFgp4BqDioJA60RTJHCnSgKiyMEpUIgWPMwFcnLLrbe_amq-OXJuuSpdTXQ_3m86lXAoQSSz5Br3Zork1zlkq0rUtV2j7lEO6sZfu7Q3s5a62y1ak9-SfrgG42gKYu7QynW2GL_8p-gUWVnXB</recordid><startdate>20130904</startdate><enddate>20130904</enddate><creator>Liu, Yongbing</creator><creator>Du, Haifeng</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20130904</creationdate><title>Metal-Free Borane-Catalyzed Highly Stereoselective Hydrogenation of Pyridines</title><author>Liu, Yongbing ; Du, Haifeng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a381t-a8cadd0521da07788ba03e5f801b00872f4d9de64cae6d0aa8b569894317b3013</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Boranes - chemistry</topic><topic>Catalysis</topic><topic>Hydrogenation</topic><topic>Molecular Structure</topic><topic>Piperidines - chemical synthesis</topic><topic>Piperidines - chemistry</topic><topic>Pyridines - chemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liu, Yongbing</creatorcontrib><creatorcontrib>Du, Haifeng</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liu, Yongbing</au><au>Du, Haifeng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Metal-Free Borane-Catalyzed Highly Stereoselective Hydrogenation of Pyridines</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2013-09-04</date><risdate>2013</risdate><volume>135</volume><issue>35</issue><spage>12968</spage><epage>12971</epage><pages>12968-12971</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><abstract>A metal-free direct hydrogenation of pyridines was successfully realized by using homogeneous borane catalysts generated from alkenes and HB(C6F5)2 via in situ hydroboration. The reaction affords a broad range of piperidines in high yields with excellent cis stereoselectivities.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>23944383</pmid><doi>10.1021/ja406761j</doi><tpages>4</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0002-7863
ispartof Journal of the American Chemical Society, 2013-09, Vol.135 (35), p.12968-12971
issn 0002-7863
1520-5126
language eng
recordid cdi_proquest_miscellaneous_1430397411
source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects Boranes - chemistry
Catalysis
Hydrogenation
Molecular Structure
Piperidines - chemical synthesis
Piperidines - chemistry
Pyridines - chemistry
Stereoisomerism
title Metal-Free Borane-Catalyzed Highly Stereoselective Hydrogenation of Pyridines
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-23T04%3A44%3A06IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Metal-Free%20Borane-Catalyzed%20Highly%20Stereoselective%20Hydrogenation%20of%20Pyridines&rft.jtitle=Journal%20of%20the%20American%20Chemical%20Society&rft.au=Liu,%20Yongbing&rft.date=2013-09-04&rft.volume=135&rft.issue=35&rft.spage=12968&rft.epage=12971&rft.pages=12968-12971&rft.issn=0002-7863&rft.eissn=1520-5126&rft_id=info:doi/10.1021/ja406761j&rft_dat=%3Cproquest_cross%3E1430397411%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a381t-a8cadd0521da07788ba03e5f801b00872f4d9de64cae6d0aa8b569894317b3013%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=1430397411&rft_id=info:pmid/23944383&rfr_iscdi=true