An Improved Synthesis of BrettPhos- and RockPhos-Type Biarylphosphine Ligands
Improved processes for the preparation of biphenyl-based phosphine ligands t-BuBrettPhos, RockPhos, and BrettPhos are presented. The new methods, featuring the use of Grignard reagents and catalytic amounts of copper, are superior to the previous methods, which require the use of tert-butyllithium a...
| Main Authors: | , |
|---|---|
| Other Authors: | |
| Format: | Article |
| Language: | en_US |
| Published: |
Wiley Blackwell
2013
|
| Online Access: | http://hdl.handle.net/1721.1/81975 https://orcid.org/0000-0003-3875-4775 |
| _version_ | 1811093059183575040 |
|---|---|
| author | Hoshiya, Naoyuki Buchwald, Stephen Leffler |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Hoshiya, Naoyuki Buchwald, Stephen Leffler |
| author_sort | Hoshiya, Naoyuki |
| collection | MIT |
| description | Improved processes for the preparation of biphenyl-based phosphine ligands t-BuBrettPhos, RockPhos, and BrettPhos are presented. The new methods, featuring the use of Grignard reagents and catalytic amounts of copper, are superior to the previous methods, which require the use of tert-butyllithium and stoichiometric amounts of copper. Specifically, the use of less dangerous reagents provides a safer process, while the use of catalytic amounts of copper allows for the isolation of pure products in high yield. These improvements are particularly significant for the large-scale preparation of these ligands. |
| first_indexed | 2024-09-23T15:38:48Z |
| format | Article |
| id | mit-1721.1/81975 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T15:38:48Z |
| publishDate | 2013 |
| publisher | Wiley Blackwell |
| record_format | dspace |
| spelling | mit-1721.1/819752022-09-29T15:13:10Z An Improved Synthesis of BrettPhos- and RockPhos-Type Biarylphosphine Ligands Hoshiya, Naoyuki Buchwald, Stephen Leffler Massachusetts Institute of Technology. Department of Chemistry Hoshiya, Naoyuki Buchwald, Stephen Leffler Improved processes for the preparation of biphenyl-based phosphine ligands t-BuBrettPhos, RockPhos, and BrettPhos are presented. The new methods, featuring the use of Grignard reagents and catalytic amounts of copper, are superior to the previous methods, which require the use of tert-butyllithium and stoichiometric amounts of copper. Specifically, the use of less dangerous reagents provides a safer process, while the use of catalytic amounts of copper allows for the isolation of pure products in high yield. These improvements are particularly significant for the large-scale preparation of these ligands. National Institutes of Health (U.S.) (GM46059) Astellas USA Foundation 2013-11-04T17:14:46Z 2013-11-04T17:14:46Z 2012-06 2012-05 Article http://purl.org/eprint/type/JournalArticle 16154150 1615-4169 http://hdl.handle.net/1721.1/81975 Hoshiya, Naoyuki, and Stephen L. Buchwald. “An Improved Synthesis of BrettPhos- and RockPhos-Type Biarylphosphine Ligands.” Advanced Synthesis & Catalysis 354, no. 10 (July 9, 2012): 2031-2037. https://orcid.org/0000-0003-3875-4775 en_US http://dx.doi.org/10.1002/adsc.201200398 Advanced Synthesis & Catalysis Creative Commons Attribution-Noncommercial-Share Alike 3.0 http://creativecommons.org/licenses/by-nc-sa/3.0/ application/pdf Wiley Blackwell PMC |
| spellingShingle | Hoshiya, Naoyuki Buchwald, Stephen Leffler An Improved Synthesis of BrettPhos- and RockPhos-Type Biarylphosphine Ligands |
| title | An Improved Synthesis of BrettPhos- and RockPhos-Type Biarylphosphine Ligands |
| title_full | An Improved Synthesis of BrettPhos- and RockPhos-Type Biarylphosphine Ligands |
| title_fullStr | An Improved Synthesis of BrettPhos- and RockPhos-Type Biarylphosphine Ligands |
| title_full_unstemmed | An Improved Synthesis of BrettPhos- and RockPhos-Type Biarylphosphine Ligands |
| title_short | An Improved Synthesis of BrettPhos- and RockPhos-Type Biarylphosphine Ligands |
| title_sort | improved synthesis of brettphos and rockphos type biarylphosphine ligands |
| url | http://hdl.handle.net/1721.1/81975 https://orcid.org/0000-0003-3875-4775 |
| work_keys_str_mv | AT hoshiyanaoyuki animprovedsynthesisofbrettphosandrockphostypebiarylphosphineligands AT buchwaldstephenleffler animprovedsynthesisofbrettphosandrockphostypebiarylphosphineligands AT hoshiyanaoyuki improvedsynthesisofbrettphosandrockphostypebiarylphosphineligands AT buchwaldstephenleffler improvedsynthesisofbrettphosandrockphostypebiarylphosphineligands |