Palladium-Catalyzed C-P Coupling Reactions between Vinyl Triflates and Phosphine-Boranes: Efficient Access to Vinylphosphine-Boranes
Delphine Julienne; Jean-François Lohier; Olivier Delacroix; Annie-Claude Gaumont; Journal of Organic Chemistry 72 (2007) 2247–2250; doi:10.1021/jo062482o

data_4022806
_publ_contact_author_address
;     Laboratoire de Chimie Mol\'eculaire et Thio-organique, UMR CNRS 6507
      ENSICAEN - Universit\'e de Caen
      14050 Caen
      France
;
_publ_contact_author_email       annie-claude.gaumont@ensicaen.fr
_publ_contact_author_fax         '332 31 45 28 65'
_publ_contact_author_name        'Gaumont, Annie-Claude'
_publ_contact_author_phone       '332 31 45 28 73'
_publ_section_title
;
 Palladium-Catalyzed C-P Coupling Reactions between Vinyl Triflates
 and Phosphine-Boranes: Efficient Access to Vinylphosphine-Boranes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2247
_journal_page_last               2250
_journal_paper_doi               10.1021/jo062482o
_journal_volume                  72
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H28 B P'
_chemical_formula_sum            'C22 H28 B P'
_chemical_formula_weight         334.22
_chemical_melting_point          400(2)
_chemical_name_systematic
;
 ((1R,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-en-2-yl)diphenylphosphineborane
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.4400(4)
_cell_length_b                   10.0459(4)
_cell_length_c                   20.4407(8)
_cell_measurement_reflns_used    8278
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.38
_cell_volume                     1938.46(14)
_computing_cell_refinement       'APEX2 software'
_computing_data_collection       'APEX2 software'
_computing_data_reduction        'APEX2 software'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Nonius ApexII-CCD'
_diffrn_measurement_method       '\w scans and \f scan with \k offsets'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0205
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            36417
_diffrn_reflns_theta_full        27.62
_diffrn_reflns_theta_max         27.62
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       polyhedron
_exptl_crystal_F_000             720
_exptl_crystal_recrystallization_method ether
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details 'Flack H D (1983), 1916 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.02(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         4474
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0310
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0602P)^2^+0.1350P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0908
_reflns_number_gt                4284
_reflns_number_total             4474
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo062482osi20061204_015339.cif
_cod_data_source_block           julienne3
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4022806