Oxidative C−C Bond-Forming Reaction of Electron-Rich Alkylbenzyl Ether with Trimethylvinyloxysilane

Name: Work Video:
Duration: 3 min 30 s
Description: Treatment of an electron-rich benzyl ether with DDQ at ambient temperature followed by addition of a silyl enol ether undergoes a C-C bond-forming reaction to afford 3-alkoxy-3-phenyl-propionyl compound. This is a general reaction and works well with a variety of silyl enol ethers to give carbonyl products in yields ranging from 10 to 85%.
Bai‐Ping Ying; Bridget G. Trogden; Daniel T. Kohlman; Sidney Liang; Yao‐Chang Xu
{'id': 'https://openalex.org/W2111534217', 'doi': 'https://doi.org/10.1021/ol036314j', 'title': 'Oxidative C−C Bond-Forming Reaction of Electron-Rich Alkylbenzyl Ether with Trimethylvinyloxysilane', 'display_name': 'Oxidative C−C Bond-Forming Reaction of Electron-Rich Alkylbenzyl Ether with Trimethylvinyloxysilane', 'publication_year': 2004, 'publication_date': '2004-04-14', 'ids': {'openalex': 'https://openalex.org/W2111534217', 'doi': 'https://doi.org/10.1021/ol036314j', 'mag': '2111534217', 'pmid': 'https://pubmed.ncbi.nlm.nih.gov/15128226'}, 'language': 'en', 'primary_location': {'is_oa': False, 'landing_page_url': 'https://doi.org/10.1021/ol036314j', 'pdf_url': None, 'source': {'id': 'https://openalex.org/S201989124', 'display_name': 'Organic Letters', 'issn_l': '1523-7052', 'issn': ['1523-7052', '1523-7060'], 'is_oa': False, 'is_in_doaj': False, 'is_core': True, 'host_organization': 'https://openalex.org/P4310320006', 'host_organization_name': 'American Chemical Society', 'host_organization_lineage': ['https://openalex.org/P4310320006'], 'host_organization_lineage_names': ['American Chemical Society'], 'type': 'journal'}, 'license': None, 'license_id': None, 'version': None, 'is_accepted': False, 'is_published': False}, 'type': 'article', 'type_crossref': 'journal-article', 'indexed_in': ['crossref', 'pubmed'], 'open_access': {'is_oa': True, 'oa_status': 'green', 'oa_url': 'https://repository.ubn.ru.nl/bitstream/handle/2066/58611/1/58611.pdf', 'any_repository_has_fulltext': True}, 'authorships': [{'author_position': 'first', 'author': {'id': 'https://openalex.org/A5108574658', 'display_name': 'Bai‐Ping Ying', 'orcid': None}, 'institutions': [{'id': 'https://openalex.org/I168537998', 'display_name': 'Eli Lilly (United States)', 'ror': 'https://ror.org/01qat3289', 'country_code': 'US', 'type': 'company', 'lineage': ['https://openalex.org/I168537998']}], 'countries': ['US'], 'is_corresponding': False, 'raw_author_name': 'Bai-Ping Ying', 'raw_affiliation_strings': ['Discovery Chemistry Research, Lilly Research Laboratories, Lilly Corporate Center, Eli Lilly and Company, Indianapolis, Indiana 46285, USA.'], 'affiliations': [{'raw_affiliation_string': 'Discovery Chemistry Research, Lilly Research Laboratories, Lilly Corporate Center, Eli Lilly and Company, Indianapolis, Indiana 46285, USA.', 'institution_ids': ['https://openalex.org/I168537998']}]}, {'author_position': 'middle', 'author': {'id': 'https://openalex.org/A5010734427', 'display_name': 'Bridget G. Trogden', 'orcid': 'https://orcid.org/0000-0001-9220-4999'}, 'institutions': [{'id': 'https://openalex.org/I168537998', 'display_name': 'Eli Lilly (United States)', 'ror': 'https://ror.org/01qat3289', 'country_code': 'US', 'type': 'company', 'lineage': ['https://openalex.org/I168537998']}], 'countries': ['US'], 'is_corresponding': False, 'raw_author_name': 'Bridget G. Trogden', 'raw_affiliation_strings': ['Discovery Chemistry Research, Lilly Research Laboratories, Lilly Corporate Center, Eli Lilly and Company, Indianapolis, Indiana 46285'], 'affiliations': [{'raw_affiliation_string': 'Discovery Chemistry Research, Lilly Research Laboratories, Lilly Corporate Center, Eli Lilly and Company, Indianapolis, Indiana 46285', 'institution_ids': ['https://openalex.org/I168537998']}]}, {'author_position': 'middle', 'author': {'id': 'https://openalex.org/A5083580933', 'display_name': 'Daniel T. Kohlman', 'orcid': None}, 'institutions': [{'id': 'https://openalex.org/I168537998', 'display_name': 'Eli Lilly (United States)', 'ror': 'https://ror.org/01qat3289', 'country_code': 'US', 'type': 'company', 'lineage': ['https://openalex.org/I168537998']}], 'countries': ['US'], 'is_corresponding': False, 'raw_author_name': 'Daniel T. Kohlman', 'raw_affiliation_strings': ['Discovery Chemistry Research, Lilly Research Laboratories, Lilly Corporate Center, Eli Lilly and Company, Indianapolis, Indiana 46285'], 'affiliations': [{'raw_affiliation_string': 'Discovery Chemistry Research, Lilly Research Laboratories, Lilly Corporate Center, Eli Lilly and Company, Indianapolis, Indiana 46285', 'institution_ids': ['https://openalex.org/I168537998']}]}, {'author_position': 'middle', 'author': {'id': 'https://openalex.org/A5109427740', 'display_name': 'Sidney Liang', 'orcid': None}, 'institutions': [{'id': 'https://openalex.org/I168537998', 'display_name': 'Eli Lilly (United States)', 'ror': 'https://ror.org/01qat3289', 'country_code': 'US', 'type': 'company', 'lineage': ['https://openalex.org/I168537998']}], 'countries': ['US'], 'is_corresponding': False, 'raw_author_name': 'Sidney X. Liang', 'raw_affiliation_strings': ['Discovery Chemistry Research, Lilly Research Laboratories, Lilly Corporate Center, Eli Lilly and Company, Indianapolis, Indiana 46285'], 'affiliations': [{'raw_affiliation_string': 'Discovery Chemistry Research, Lilly Research Laboratories, Lilly Corporate Center, Eli Lilly and Company, Indianapolis, Indiana 46285', 'institution_ids': ['https://openalex.org/I168537998']}]}, {'author_position': 'last', 'author': {'id': 'https://openalex.org/A5109469745', 'display_name': 'Yao‐Chang Xu', 'orcid': None}, 'institutions': [{'id': 'https://openalex.org/I168537998', 'display_name': 'Eli Lilly (United States)', 'ror': 'https://ror.org/01qat3289', 'country_code': 'US', 'type': 'company', 'lineage': ['https://openalex.org/I168537998']}], 'countries': ['US'], 'is_corresponding': False, 'raw_author_name': 'Yao-Chang Xu', 'raw_affiliation_strings': ['Discovery Chemistry Research, Lilly Research Laboratories, Lilly Corporate Center, Eli Lilly and Company, Indianapolis, Indiana 46285'], 'affiliations': [{'raw_affiliation_string': 'Discovery Chemistry Research, Lilly Research Laboratories, Lilly Corporate Center, Eli Lilly and Company, Indianapolis, Indiana 46285', 'institution_ids': ['https://openalex.org/I168537998']}]}], 'institution_assertions': [], 'countries_distinct_count': 1, 'institutions_distinct_count': 1, 'corresponding_author_ids': [], 'corresponding_institution_ids': [], 'apc_list': None, 'apc_paid': None, 'fwci': 1.3, 'has_fulltext': True, 'fulltext_origin': 'pdf', 'cited_by_count': 80, 'citation_normalized_percentile': {'value': 0.908743, 'is_in_top_1_percent': False, 'is_in_top_10_percent': True}, 'cited_by_percentile_year': {'min': 95, 'max': 96}, 'biblio': {'volume': '6', 'issue': '10', 'first_page': '1523', 'last_page': '1526'}, 'is_retracted': False, 'is_paratext': False, 'primary_topic': {'id': 'https://openalex.org/T10835', 'display_name': 'Carbohydrate Chemistry and Synthesis', 'score': 0.9999, 'subfield': {'id': 'https://openalex.org/subfields/1605', 'display_name': 'Organic Chemistry'}, 'field': {'id': 'https://openalex.org/fields/16', 'display_name': 'Chemistry'}, 'domain': {'id': 'https://openalex.org/domains/3', 'display_name': 'Physical Sciences'}}, 'topics': [{'id': 'https://openalex.org/T10835', 'display_name': 'Carbohydrate Chemistry and Synthesis', 'score': 0.9999, 'subfield': {'id': 'https://openalex.org/subfields/1605', 'display_name': 'Organic Chemistry'}, 'field': {'id': 'https://openalex.org/fields/16', 'display_name': 'Chemistry'}, 'domain': {'id': 'https://openalex.org/domains/3', 'display_name': 'Physical Sciences'}}, {'id': 'https://openalex.org/T10911', 'display_name': 'Chemical Synthesis and Analysis', 'score': 0.999, 'subfield': {'id': 'https://openalex.org/subfields/1312', 'display_name': 'Molecular Biology'}, 'field': {'id': 'https://openalex.org/fields/13', 'display_name': 'Biochemistry, Genetics and Molecular Biology'}, 'domain': {'id': 'https://openalex.org/domains/1', 'display_name': 'Life Sciences'}}, {'id': 'https://openalex.org/T11831', 'display_name': 'Chemical Synthesis and Reactions', 'score': 0.9988, 'subfield': {'id': 'https://openalex.org/subfields/1605', 'display_name': 'Organic Chemistry'}, 'field': {'id': 'https://openalex.org/fields/16', 'display_name': 'Chemistry'}, 'domain': {'id': 'https://openalex.org/domains/3', 'display_name': 'Physical Sciences'}}], 'keywords': [{'id': 'https://openalex.org/keywords/silyl-enol-ether', 'display_name': 'Silyl enol ether', 'score': 0.728442}, {'id': 'https://openalex.org/keywords/enol-ether', 'display_name': 'Enol ether', 'score': 0.50624675}, {'id': 'https://openalex.org/keywords/silyl-ether', 'display_name': 'Silyl ether', 'score': 0.45052582}], 'concepts': [{'id': 'https://openalex.org/C185592680', 'wikidata': 'https://www.wikidata.org/wiki/Q2329', 'display_name': 'Chemistry', 'level': 0, 'score': 0.9326861}, {'id': 'https://openalex.org/C2780407432', 'wikidata': 'https://www.wikidata.org/wiki/Q103230', 'display_name': 'Ether', 'level': 2, 'score': 0.7627368}, {'id': 'https://openalex.org/C90150868', 'wikidata': 'https://www.wikidata.org/wiki/Q39513', 'display_name': 'Alkoxy group', 'level': 3, 'score': 0.74379057}, {'id': 'https://openalex.org/C2778491686', 'wikidata': 'https://www.wikidata.org/wiki/Q2501461', 'display_name': 'Silyl enol ether', 'level': 4, 'score': 0.728442}, {'id': 'https://openalex.org/C5304478', 'wikidata': 'https://www.wikidata.org/wiki/Q502457', 'display_name': 'Silylation', 'level': 3, 'score': 0.6997187}, {'id': 'https://openalex.org/C2777495281', 'wikidata': 'https://www.wikidata.org/wiki/Q408053', 'display_name': 'Enol', 'level': 3, 'score': 0.6144769}, {'id': 'https://openalex.org/C155647269', 'wikidata': 'https://www.wikidata.org/wiki/Q243455', 'display_name': 'Medicinal chemistry', 'level': 1, 'score': 0.55572766}, {'id': 'https://openalex.org/C2781200603', 'wikidata': 'https://www.wikidata.org/wiki/Q420217', 'display_name': 'Enol ether', 'level': 3, 'score': 0.50624675}, {'id': 'https://openalex.org/C2780741609', 'wikidata': 'https://www.wikidata.org/wiki/Q419032', 'display_name': 'Silyl ether', 'level': 4, 'score': 0.45052582}, {'id': 'https://openalex.org/C57600042', 'wikidata': 'https://www.wikidata.org/wiki/Q227564', 'display_name': 'Oxidative phosphorylation', 'level': 2, 'score': 0.41912988}, {'id': 'https://openalex.org/C75473681', 'wikidata': 'https://www.wikidata.org/wiki/Q188651', 'display_name': 'Photochemistry', 'level': 1, 'score': 0.35332644}, {'id': 'https://openalex.org/C178790620', 'wikidata': 'https://www.wikidata.org/wiki/Q11351', 'display_name': 'Organic chemistry', 'level': 1, 'score': 0.34199744}, {'id': 'https://openalex.org/C161790260', 'wikidata': 'https://www.wikidata.org/wiki/Q82264', 'display_name': 'Catalysis', 'level': 2, 'score': 0.22382706}, {'id': 'https://openalex.org/C2780263894', 'wikidata': 'https://www.wikidata.org/wiki/Q335268', 'display_name': 'Alkyl', 'level': 2, 'score': 0.106564134}, {'id': 'https://openalex.org/C55493867', 'wikidata': 'https://www.wikidata.org/wiki/Q7094', 'display_name': 'Biochemistry', 'level': 1, 'score': 0.0}], 'mesh': [], 'locations_count': 4, 'locations': [{'is_oa': False, 'landing_page_url': 'https://doi.org/10.1021/ol036314j', 'pdf_url': None, 'source': {'id': 'https://openalex.org/S201989124', 'display_name': 'Organic Letters', 'issn_l': '1523-7052', 'issn': ['1523-7052', '1523-7060'], 'is_oa': False, 'is_in_doaj': False, 'is_core': True, 'host_organization': 'https://openalex.org/P4310320006', 'host_organization_name': 'American Chemical Society', 'host_organization_lineage': ['https://openalex.org/P4310320006'], 'host_organization_lineage_names': ['American Chemical Society'], 'type': 'journal'}, 'license': None, 'license_id': None, 'version': None, 'is_accepted': False, 'is_published': False}, {'is_oa': True, 'landing_page_url': 'http://hdl.handle.net/2066/58611', 'pdf_url': 'https://repository.ubn.ru.nl/bitstream/handle/2066/58611/1/58611.pdf', 'source': {'id': 'https://openalex.org/S4306401067', 'display_name': 'Radboud Repository (Radboud University)', 'issn_l': None, 'issn': None, 'is_oa': True, 'is_in_doaj': False, 'is_core': False, 'host_organization': 'https://openalex.org/I145872427', 'host_organization_name': 'Radboud University Nijmegen', 'host_organization_lineage': ['https://openalex.org/I145872427'], 'host_organization_lineage_names': ['Radboud University Nijmegen'], 'type': 'repository'}, 'license': 'other-oa', 'license_id': 'https://openalex.org/licenses/other-oa', 'version': 'publishedVersion', 'is_accepted': True, 'is_published': True}, {'is_oa': True, 'landing_page_url': 'https://repository.ubn.ru.nl//bitstream/handle/2066/58611/58611.pdf', 'pdf_url': 'https://repository.ubn.ru.nl//bitstream/handle/2066/58611/58611.pdf', 'source': {'id': 'https://openalex.org/S4306401067', 'display_name': 'Radboud Repository (Radboud University)', 'issn_l': None, 'issn': None, 'is_oa': True, 'is_in_doaj': False, 'is_core': False, 'host_organization': 'https://openalex.org/I145872427', 'host_organization_name': 'Radboud University Nijmegen', 'host_organization_lineage': ['https://openalex.org/I145872427'], 'host_organization_lineage_names': ['Radboud University Nijmegen'], 'type': 'repository'}, 'license': None, 'license_id': None, 'version': 'publishedVersion', 'is_accepted': True, 'is_published': True}, {'is_oa': False, 'landing_page_url': 'https://pubmed.ncbi.nlm.nih.gov/15128226', 'pdf_url': None, 'source': {'id': 'https://openalex.org/S4306525036', 'display_name': 'PubMed', 'issn_l': None, 'issn': None, 'is_oa': False, 'is_in_doaj': False, 'is_core': False, 'host_organization': 'https://openalex.org/I1299303238', 'host_organization_name': 'National Institutes of Health', 'host_organization_lineage': ['https://openalex.org/I1299303238'], 'host_organization_lineage_names': ['National Institutes of Health'], 'type': 'repository'}, 'license': None, 'license_id': None, 'version': None, 'is_accepted': False, 'is_published': False}], 'best_oa_location': {'is_oa': True, 'landing_page_url': 'http://hdl.handle.net/2066/58611', 'pdf_url': 'https://repository.ubn.ru.nl/bitstream/handle/2066/58611/1/58611.pdf', 'source': {'id': 'https://openalex.org/S4306401067', 'display_name': 'Radboud Repository (Radboud University)', 'issn_l': None, 'issn': None, 'is_oa': True, 'is_in_doaj': False, 'is_core': False, 'host_organization': 'https://openalex.org/I145872427', 'host_organization_name': 'Radboud University Nijmegen', 'host_organization_lineage': ['https://openalex.org/I145872427'], 'host_organization_lineage_names': ['Radboud University Nijmegen'], 'type': 'repository'}, 'license': 'other-oa', 'license_id': 'https://openalex.org/licenses/other-oa', 'version': 'publishedVersion', 'is_accepted': True, 'is_published': True}, 'sustainable_development_goals': [], 'grants': [], 'datasets': [], 'versions': [], 'referenced_works_count': 3, 'referenced_works': ['https://openalex.org/W1966054630', 'https://openalex.org/W2949415058', 'https://openalex.org/W2952943188'], 'related_works': ['https://openalex.org/W4205292667', 'https://openalex.org/W3044089388', 'https://openalex.org/W2983342871', 'https://openalex.org/W2951312441', 'https://openalex.org/W2950115803', 'https://openalex.org/W2798137214', 'https://openalex.org/W2122805670', 'https://openalex.org/W2072929627', 'https://openalex.org/W2040574782', 'https://openalex.org/W1970442421'], 'abstract_inverted_index': {'Treatment': [0], 'of': [1, 14, 39], 'an': [2], 'electron-rich': [3], 'benzyl': [4], 'ether': [5, 18], 'with': [6, 36], 'DDQ': [7], 'at': [8], 'ambient': [9], 'temperature': [10], 'followed': [11], 'by': [12], 'addition': [13], 'a': [15, 20, 30, 37], 'silyl': [16, 40], 'enol': [17, 41], 'undergoes': [19], 'C-C': [21], 'bond-forming': [22], 'reaction': [23, 32], 'to': [24, 43, 52], 'afford': [25], '3-alkoxy-3-phenyl-propionyl': [26], 'compound.': [27], 'This': [28], 'is': [29], 'general': [31], 'and': [33], 'works': [34], 'well': [35], 'variety': [38], 'ethers': [42], 'give': [44], 'carbonyl': [45], 'products': [46], 'in': [47], 'yields': [48], 'ranging': [49], 'from': [50], '10': [51], '85%.': [53]}, 'cited_by_api_url': 'https://api.openalex.org/works?filter=cites:W2111534217', 'counts_by_year': [{'year': 2022, 'cited_by_count': 1}, {'year': 2021, 'cited_by_count': 4}, {'year': 2020, 'cited_by_count': 2}, {'year': 2019, 'cited_by_count': 2}, {'year': 2018, 'cited_by_count': 4}, {'year': 2017, 'cited_by_count': 4}, {'year': 2016, 'cited_by_count': 1}, {'year': 2015, 'cited_by_count': 7}, {'year': 2014, 'cited_by_count': 3}, {'year': 2013, 'cited_by_count': 7}, {'year': 2012, 'cited_by_count': 7}], 'updated_date': '2024-12-09T21:09:02.668516', 'created_date': '2016-06-24'}
Publication Information

Basic Information

Access and Citation

AI Researcher Chatbot

Primary Location

Authors

Topics

Keywords

Related Works
