{"id":714,"date":"2020-04-23T22:30:59","date_gmt":"2020-04-24T02:30:59","guid":{"rendered":"https:\/\/sites.miamioh.edu\/undergraduate-research-forum\/?p=714"},"modified":"2020-04-27T16:24:54","modified_gmt":"2020-04-27T20:24:54","slug":"poster-copper-catalyzed-deaminative-difluoromethylation","status":"publish","type":"post","link":"https:\/\/sites.miamioh.edu\/undergraduate-research-forum\/poster-copper-catalyzed-deaminative-difluoromethylation\/","title":{"rendered":"B29: Copper-Catalyzed Deaminative Difluoromethylation"},"content":{"rendered":"<p dir=\"ltr\">A difluoromethyl group (CF2H) is considered to be a lipophilic and metabolically stable bioisostere of an amino (NH2) group. Therefore, methods that can directly convert a NH2 group into a CF2H group would be of great value to medicinal chemistry. We report an efficient Cu-catalyzed approach for the conversion of alkyl pyridinium salts, which can be readily synthesized from the corresponding alkyl amines, to their alkyl difluoromethane analogues. This protocol tolerates a broad range of functional groups and can be applied to late-stage modification of complex amino-containing pharmaceuticals.<\/p>\n<p><strong>Authors:<\/strong> Samson B. Zacate<\/p>\n<p dir=\"ltr\"><strong>Faculty Advisor:<\/strong> Dr. Wei Liu, Chemistry and Biochemistry<\/p>\n<p dir=\"ltr\">Xiaojun Zeng, Wenhao Yan, Aijie Cai, Yufei Wang, Dongqi Yang, Kundi Yang, Wei Liu<\/p>\n<p><a href=\"https:\/\/i0.wp.com\/sites.miamioh.edu\/undergraduate-research-forum\/files\/2020\/04\/B29Slide1.png\" rel=\"attachment wp-att-715\"><img data-recalc-dims=\"1\" loading=\"lazy\" decoding=\"async\" data-attachment-id=\"715\" data-permalink=\"https:\/\/sites.miamioh.edu\/undergraduate-research-forum\/poster-copper-catalyzed-deaminative-difluoromethylation\/b29slide1\/\" data-orig-file=\"https:\/\/i0.wp.com\/sites.miamioh.edu\/undergraduate-research-forum\/files\/2020\/04\/B29Slide1.png?fit=5376%2C4032&amp;ssl=1\" data-orig-size=\"5376,4032\" data-comments-opened=\"0\" data-image-meta=\"{&quot;aperture&quot;:&quot;0&quot;,&quot;credit&quot;:&quot;&quot;,&quot;camera&quot;:&quot;&quot;,&quot;caption&quot;:&quot;&quot;,&quot;created_timestamp&quot;:&quot;0&quot;,&quot;copyright&quot;:&quot;&quot;,&quot;focal_length&quot;:&quot;0&quot;,&quot;iso&quot;:&quot;0&quot;,&quot;shutter_speed&quot;:&quot;0&quot;,&quot;title&quot;:&quot;&quot;,&quot;orientation&quot;:&quot;0&quot;}\" data-image-title=\"B29Slide1\" data-image-description=\"\" data-image-caption=\"\" data-large-file=\"https:\/\/i0.wp.com\/sites.miamioh.edu\/undergraduate-research-forum\/files\/2020\/04\/B29Slide1.png?fit=770%2C578&amp;ssl=1\" class=\"alignleft wp-image-715 size-large\" title=\"b29slide1-png\" src=\"https:\/\/i0.wp.com\/sites.miamioh.edu\/undergraduate-research-forum\/files\/2020\/04\/B29Slide1.png?resize=770%2C578\" alt=\"\" width=\"770\" height=\"578\" srcset=\"https:\/\/i0.wp.com\/sites.miamioh.edu\/undergraduate-research-forum\/files\/2020\/04\/B29Slide1.png?resize=1024%2C768&amp;ssl=1 1024w, https:\/\/i0.wp.com\/sites.miamioh.edu\/undergraduate-research-forum\/files\/2020\/04\/B29Slide1.png?resize=300%2C225&amp;ssl=1 300w, https:\/\/i0.wp.com\/sites.miamioh.edu\/undergraduate-research-forum\/files\/2020\/04\/B29Slide1.png?resize=768%2C576&amp;ssl=1 768w, https:\/\/i0.wp.com\/sites.miamioh.edu\/undergraduate-research-forum\/files\/2020\/04\/B29Slide1.png?resize=600%2C450&amp;ssl=1 600w, https:\/\/i0.wp.com\/sites.miamioh.edu\/undergraduate-research-forum\/files\/2020\/04\/B29Slide1.png?w=1540 1540w, https:\/\/i0.wp.com\/sites.miamioh.edu\/undergraduate-research-forum\/files\/2020\/04\/B29Slide1.png?w=2310 2310w\" sizes=\"auto, (max-width: 770px) 100vw, 770px\" \/><\/a><\/p>\n","protected":false},"excerpt":{"rendered":"<p>A difluoromethyl group (CF2H) is considered to be a lipophilic and metabolically stable bioisostere of an amino (NH2) group. Therefore, methods that can directly convert a NH2 group into a CF2H group would be of great value to medicinal chemistry. We report an efficient Cu-catalyzed approach for the conversion of alkyl pyridinium salts, which can [&hellip;]<\/p>\n","protected":false},"author":2899,"featured_media":0,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"_bbp_topic_count":0,"_bbp_reply_count":0,"_bbp_total_topic_count":0,"_bbp_total_reply_count":0,"_bbp_voice_count":0,"_bbp_anonymous_reply_count":0,"_bbp_topic_count_hidden":0,"_bbp_reply_count_hidden":0,"_bbp_forum_subforum_count":0,"_jetpack_newsletter_access":"","_jetpack_dont_email_post_to_subs":false,"_jetpack_newsletter_tier_id":0,"_jetpack_memberships_contains_paywalled_content":false,"_jetpack_feature_clip_id":0,"_jetpack_memberships_contains_paid_content":false,"footnotes":"","jetpack_publicize_message":"","jetpack_publicize_feature_enabled":true,"jetpack_social_post_already_shared":true,"jetpack_social_options":{"image_generator_settings":{"template":"highway","default_image_id":0,"font":"","enabled":false},"version":2},"jetpack_post_was_ever_published":false},"categories":[10,27],"tags":[195,89,194],"class_list":["post-714","post","type-post","status-publish","format-standard","hentry","category-2020-posters","category-chemistry-biochemistry","tag-catalysis","tag-stem","tag-synthesis"],"jetpack_publicize_connections":[],"jetpack_featured_media_url":"","jetpack_sharing_enabled":true,"jetpack_shortlink":"https:\/\/wp.me\/pbRpLx-bw","jetpack_likes_enabled":true,"_links":{"self":[{"href":"https:\/\/sites.miamioh.edu\/undergraduate-research-forum\/wp-json\/wp\/v2\/posts\/714","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/sites.miamioh.edu\/undergraduate-research-forum\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/sites.miamioh.edu\/undergraduate-research-forum\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/sites.miamioh.edu\/undergraduate-research-forum\/wp-json\/wp\/v2\/users\/2899"}],"replies":[{"embeddable":true,"href":"https:\/\/sites.miamioh.edu\/undergraduate-research-forum\/wp-json\/wp\/v2\/comments?post=714"}],"version-history":[{"count":0,"href":"https:\/\/sites.miamioh.edu\/undergraduate-research-forum\/wp-json\/wp\/v2\/posts\/714\/revisions"}],"wp:attachment":[{"href":"https:\/\/sites.miamioh.edu\/undergraduate-research-forum\/wp-json\/wp\/v2\/media?parent=714"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/sites.miamioh.edu\/undergraduate-research-forum\/wp-json\/wp\/v2\/categories?post=714"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/sites.miamioh.edu\/undergraduate-research-forum\/wp-json\/wp\/v2\/tags?post=714"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}