{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,2]],"date-time":"2026-09-02T23:01:33Z","timestamp":1788390093542,"version":"build-2803163510"},"reference-count":226,"publisher":"Wiley","issue":"50","license":[{"start":{"date-parts":[[2012,10,18]],"date-time":"2012-10-18T00:00:00Z","timestamp":1350518400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2012,12,7]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>We report three transformations: 1)\u2005direct transformation from biarylmethanols into biarylmethylamines; 2)\u2005direct transformation from one biarylmethanol into another biarylmethanol; 3)\u2005direct transformation from allylic alcohols into allylic amines. These transformations are based on pyridyl\u2010directed Rh\u2010catalyzed C\uf8ffC bond cleavage of secondary alcohols and subsequent addition to C\uf8feX (X=N or O) double bonds. The reaction conditions are simple and no additive is required. The driving force of C\uf8ffC bond cleavage is the formation of the stable rhodacycle intermediate. Other directing groups, such as the pyrazolyl group, can also be used although it is not as efficient as the pyridyl group. We carried out in\u2010depth investigations for transformation 1 and found that: 1)\u2005the substrate scope was broad and electron\u2010rich alcohols and electron\u2010deficient imines are more efficient; 2)\u2005as the leaving group, aldehyde had no significant impact on either the C\uf8ffC bond cleavage or the whole transformation; 3)\u2005mechanistic studies (intermediate isolation, in situ NMR spectroscopic studies, competing reactions, isotopic labeling experiments) implied that: i)\u2005The C\uf8ffC cleavage was very efficient under these conditions; ii)\u2005there is an equilibrium between the rhodacycle intermediate and the protonated byproduct phenylpyridine; iii)\u2005the addition step of the rhodacycle intermediate to imines was slower than the C\uf8ffC cleavage and the equilibrium between the rhodacycle and phenylpyridine; iv)\u2005the whole transformation was a combination of two sequences of C\uf8ffC cleavage\/nucleophilic addition and C\uf8ffC cleavage\/protonation\/C\uf8ffH activation\/nucleophilic addition, with the latter being perhaps the main pathway. We also demonstrated the first example of cleavage of an C(alkenyl)\uf8ffC(benzyl) bond. These transformations showed the exchange (or substitution) of the alcohol group with either an amine or another alcohol group. Like the \u201cgroup transplant\u201d, this method offers a new concept that can be used to directly synthesize the desired products from other chemicals through reorganization of carbon skeletons.<\/jats:p>","DOI":"10.1002\/chem.201201867","type":"journal-article","created":{"date-parts":[[2012,10,18]],"date-time":"2012-10-18T18:05:54Z","timestamp":1350583554000},"page":"16214-16225","source":"Crossref","is-referenced-by-count":57,"title":["Rh\u2010Catalyzed C\uf8ffC Cleavage of Benzyl\/Allylic Alcohols to Produce Benzyl\/Allylic Amines or other Alcohols by Nucleophilic Addition of Intermediate Rhodacycles to Aldehydes and Imines"],"prefix":"10.1002","volume":"18","author":[{"given":"Xi\u2010Sha","family":"Zhang","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yang","family":"Li","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hu","family":"Li","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kang","family":"Chen","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhi\u2010Quan","family":"Lei","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhang\u2010Jie","family":"Shi","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2012,10,18]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"For Grignard Reagents see:"},{"key":"e_1_2_6_2_2","doi-asserted-by":"crossref","unstructured":"G.\u2005S. 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Substitution reactions of propargylic amines through C\uf8ffC cleavage of propargylic amines:"},{"key":"e_1_2_6_122_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja9109055"},{"key":"e_1_2_6_123_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol100481h"},{"key":"e_1_2_6_124_2","unstructured":"For selected natural product and complex molecule synthesis examples by C\uf8ffC cleavage see:"},{"key":"e_1_2_6_125_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol061359g"},{"key":"e_1_2_6_126_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja075141g"},{"key":"e_1_2_6_127_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200903189"},{"key":"e_1_2_6_127_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200903189"},{"key":"e_1_2_6_128_2","doi-asserted-by":"publisher","DOI":"10.1039\/c1cc11005e"},{"key":"e_1_2_6_129_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar00080a002"},{"key":"e_1_2_6_130_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja993108r"},{"key":"e_1_2_6_131_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja021062n"},{"key":"e_1_2_6_132_2","unstructured":"For C\uf8ffC activation driven by release of ring strain in cyclopropane and cyclobutane derivatives see:"},{"key":"e_1_2_6_133_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja993023q"},{"key":"e_1_2_6_134_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja002885k"},{"key":"e_1_2_6_135_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0260521"},{"key":"e_1_2_6_136_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja017460s"},{"key":"e_1_2_6_137_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0703170"},{"key":"e_1_2_6_138_2","doi-asserted-by":"publisher","DOI":"10.1021\/om7012524"},{"key":"e_1_2_6_139_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja7111299"},{"key":"e_1_2_6_140_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol802218a"},{"key":"e_1_2_6_141_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200902593"},{"key":"e_1_2_6_142_2","doi-asserted-by":"publisher","DOI":"10.1039\/b904405a"},{"key":"e_1_2_6_143_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol900829c"},{"key":"e_1_2_6_144_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja101469t"},{"key":"e_1_2_6_145_2","unstructured":"For C\uf8ffC activation driven by forming stable metallacycle or \u03c0\u2010allyl metal complex as intermediates in the assistance of coordination see:"},{"key":"e_1_2_6_146_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja983197s"},{"key":"e_1_2_6_147_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja992048m"},{"key":"e_1_2_6_148_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja9049564"},{"key":"e_1_2_6_149_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200902215"},{"key":"e_1_2_6_149_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200902215"},{"key":"e_1_2_6_150_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja980714y"},{"key":"e_1_2_6_151_2","doi-asserted-by":"publisher","DOI":"10.1039\/b708526e"},{"key":"e_1_2_6_152_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2008.09.118"},{"key":"e_1_2_6_153_2","unstructured":"For C\uf8ffC activation driven by forming stable C\uf8ffMetal bonds as intermediates mainly in high energy tertiary alcohols see:"},{"key":"e_1_2_6_154_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo0344034"},{"key":"e_1_2_6_155_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0348405"},{"key":"e_1_2_6_156_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo049031t"},{"key":"e_1_2_6_157_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja076346s"},{"key":"e_1_2_6_158_2","unstructured":"For C\uf8ffC activation driven by other methods see:"},{"key":"e_1_2_6_159_2","doi-asserted-by":"publisher","DOI":"10.1021\/om00027a054"},{"key":"e_1_2_6_160_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja055452w"},{"key":"e_1_2_6_161_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja047320t"},{"key":"e_1_2_6_162_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1128684"},{"key":"e_1_2_6_163_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200700902"},{"key":"e_1_2_6_163_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200700902"},{"key":"e_1_2_6_164_2","unstructured":"For competing oxidation reactions of secondary alcohols to ketones via \u03b2\u2010H elimination see:"},{"key":"e_1_2_6_165_2","volume-title":"Metal\u2010Catalyzed Oxidations of Organic Compounds","author":"Sheldon R. A.","year":"1984"},{"key":"e_1_2_6_166_2","volume-title":"Oxidations in Organic Chemistry","author":"Hudlicky M.","year":"1990"},{"key":"e_1_2_6_167_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.274.5295.2044"},{"key":"e_1_2_6_168_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar010075n"},{"key":"e_1_2_6_169_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar040243m"},{"key":"e_1_2_6_170_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo971268k"},{"key":"e_1_2_6_171_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo010338r"},{"key":"e_1_2_6_172_2","doi-asserted-by":"publisher","DOI":"10.1039\/b303160h"},{"key":"e_1_2_6_173_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol062806v"},{"key":"e_1_2_6_174_2","doi-asserted-by":"publisher","DOI":"10.1021\/om010087c"},{"key":"e_1_2_6_175_2","unstructured":"For reviews on transition metal (Rh included) catalyzed C\uf8ffC activation see:"},{"key":"e_1_2_6_176_2","first-page":"10","volume-title":"Sensors Update","author":"Grate J. W.","year":"1996"},{"key":"e_1_2_6_177_2","doi-asserted-by":"publisher","DOI":"10.1039\/B308864M"},{"key":"e_1_2_6_178_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar700133y"},{"key":"e_1_2_6_179_2","doi-asserted-by":"publisher","DOI":"10.2174\/138527207782418645"},{"key":"e_1_2_6_180_2","doi-asserted-by":"publisher","DOI":"10.1039\/C0CC02566F"},{"key":"e_1_2_6_181_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0732779"},{"key":"e_1_2_6_182_2","unstructured":"For C\uf8ffC activation of strained rings catalyzed by Rh catalysts see:"},{"key":"e_1_2_6_183_2","doi-asserted-by":"publisher","DOI":"10.1080\/00397919408011750"},{"key":"e_1_2_6_184_2","doi-asserted-by":"publisher","DOI":"10.1038\/370540a0"},{"key":"e_1_2_6_185_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja9604525"},{"key":"e_1_2_6_186_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol990599b"},{"key":"e_1_2_6_187_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20000717)112:14<2600::AID-ANGE2600>3.0.CO;2-N"},{"key":"e_1_2_6_187_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20000717)39:14<2484::AID-ANIE2484>3.0.CO;2-1"},{"key":"e_1_2_6_188_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja001483"},{"key":"e_1_2_6_189_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja028912j"},{"key":"e_1_2_6_190_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol049833a"},{"key":"e_1_2_6_191_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200804281"},{"key":"e_1_2_6_191_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200804281"},{"key":"e_1_2_6_192_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200904527"},{"key":"e_1_2_6_192_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200904527"},{"key":"e_1_2_6_193_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja110039h"},{"key":"e_1_2_6_194_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja804992n"},{"key":"e_1_2_6_195_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00275a086"},{"key":"e_1_2_6_195_3","doi-asserted-by":"publisher","DOI":"10.1021\/ja0033537"},{"key":"e_1_2_6_196_2","unstructured":"For C\uf8ffC activation of tertairy alcohols catalyzed by Rh catalysts: see refs.\u2005[34e] and [35c]."},{"key":"e_1_2_6_197_2","unstructured":"For C\uf8ffC activation of secondary alcohols catalyzed by Rh catalysts see refs.\u2005[38] and [24\u2009a]."},{"key":"e_1_2_6_198_2","doi-asserted-by":"publisher","DOI":"10.1039\/a800537k"},{"key":"e_1_2_6_198_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20020816)114:16<3157::AID-ANGE3157>3.0.CO;2-M"},{"key":"e_1_2_6_198_4","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20020816)41:16<3031::AID-ANIE3031>3.0.CO;2-X"},{"key":"e_1_2_6_199_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr0505268"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.201201867","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.201201867","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T19:31:06Z","timestamp":1760297466000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.201201867"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2012,10,18]]},"references-count":226,"journal-issue":{"issue":"50","published-print":{"date-parts":[[2012,12,7]]}},"alternative-id":["10.1002\/chem.201201867"],"URL":"https:\/\/doi.org\/10.1002\/chem.201201867","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2012,10,18]]}}}